diff --git a/.github/py-shiny/setup/action.yaml b/.github/py-shiny/setup/action.yaml
index e96f99619..63b1e86e2 100644
--- a/.github/py-shiny/setup/action.yaml
+++ b/.github/py-shiny/setup/action.yaml
@@ -17,15 +17,10 @@ runs:
           # cache-dependency-path: |
           #   setup.cfg
 
-      - name: Upgrade pip
-        shell: bash
-        run: python -m pip install --upgrade pip
-
       - name: Install dependencies
         shell: bash
         run: |
-          pip install https://github.com/rstudio/py-htmltools/tarball/main
-          make install-deps
+          make install-ci
 
       - name: Install
         shell: bash
diff --git a/.github/workflows/build-docs.yaml b/.github/workflows/build-docs.yaml
index 7cc001a61..5929db954 100644
--- a/.github/workflows/build-docs.yaml
+++ b/.github/workflows/build-docs.yaml
@@ -23,30 +23,15 @@ jobs:
         with:
           python-version: ${{ matrix.python-version }}
 
-      - name: Upgrade pip
-        run: python -m pip install --upgrade pip
-
       - name: Install Quarto
         uses: quarto-dev/quarto-actions/setup@v2
         with:
           version: 1.3.340
 
-      - name: Install dependencies
-        run: |
-          cd docs
-          make ../venv
-          make deps
-
-      - name: Run quartodoc
-        run: |
-          cd docs
-          make quartodoc
-
       - name: Build site
         if: ${{ github.event_name != 'pull_request' || startsWith(github.head_ref, 'docs')  }}
         run: |
-          cd docs
-          make site
+          make docs-site
 
       - name: Upload site artifact
         if: github.ref == 'refs/heads/main'
diff --git a/.github/workflows/pytest.yaml b/.github/workflows/pytest.yaml
index ddc857c25..a75b7c46d 100644
--- a/.github/workflows/pytest.yaml
+++ b/.github/workflows/pytest.yaml
@@ -220,9 +220,7 @@ jobs:
           python-version: "3.10"
       - name: Install dependencies
         run: |
-          python -m pip install --upgrade pip
-          pip install https://github.com/rstudio/py-htmltools/tarball/main
-          make install-deps
+          make install-ci
           make install
       - name: "Build Package"
         run: |
diff --git a/Makefile b/Makefile
index 0f183acfa..7f0d5d636 100644
--- a/Makefile
+++ b/Makefile
@@ -2,7 +2,7 @@
 # Prerequisites of .PHONY are always interpreted as literal target names, never as patterns (even if they contain ‘%’ characters).
 # # .PHONY: help clean% check% format% docs% lint test pyright playwright% install% testrail% coverage release js-*
 # Using `FORCE` as prerequisite to _force_ the target to always run; https://www.gnu.org/software/make/manual/make.html#index-FORCE
-FORCE: ;
+FORCE:
 
 .DEFAULT_GOAL := help
 
@@ -26,11 +26,150 @@ for line in sys.stdin:
 endef
 export PRINT_HELP_PYSCRIPT
 
-BROWSER := python -c "$$BROWSER_PYSCRIPT"
+
+BROWSER := $(PYTHON) -c "$$BROWSER_PYSCRIPT"
 
 help: FORCE
-	@python -c "$$PRINT_HELP_PYSCRIPT" < $(MAKEFILE_LIST)
+	@python3 -c "$$PRINT_HELP_PYSCRIPT" < $(MAKEFILE_LIST)
+
+
+# Gather python3 version; Ex: `3.11`
+PYTHON_VERSION := $(shell python3 -c "from platform import python_version; print(python_version().rsplit('.', 1)[0])")
+
+# -----------------
+# File paths for common executables / paths
+# -----------------
+
+VENV = .venv
+# VENV = .venv-$(PYTHON_VERSION)
+PYBIN = $(VENV)/bin
+PIP = $(PYBIN)/pip
+PYTHON = $(PYBIN)/python
+SITE_PACKAGES=$(VENV)/lib/python$(PYTHON_VERSION)/site-packages
+
+# -----------------
+# Core virtual environment and installing
+# -----------------
+
+# Any targets that depend on $(VENV) or $(PYBIN) will cause the venv to be
+# created. To use the venv, python scripts should run with the prefix $(PYBIN),
+# as in `$(PYBIN)/pip`.
+$(VENV):
+	@echo "-------- Making virtual environment: $(VENV) --------"
+	python3 -m venv $(VENV)
+	$(PYBIN)/pip install --upgrade pip
+
+$(PYBIN): $(VENV)
+$(PYTHON): $(PYBIN)
+$(PIP): $(PYBIN)
+
+UV = $(SITE_PACKAGES)/uv
+$(UV):
+	$(MAKE) $(PYBIN)
+	@echo "-------- Installing uv --------"
+	. $(PYBIN)/activate && \
+	  pip install uv
+
+
+# -----------------
+# Python package executables
+# -----------------
+# Use `FOO=$(PYBIN)/foo` to define the path to a package's executable
+# Depend on `$(FOO)` to ensure the package is installed,
+# but use `$(PYBIN)/foo` to actually run the package's executable
+BLACK = $(SITE_PACKAGES)/black
+ISORT = $(SITE_PACKAGES)/isort
+FLAKE8 = $(SITE_PACKAGES)/flake8
+PYTEST = $(SITE_PACKAGES)/pytest
+COVERAGE = $(SITE_PACKAGES)/coverage
+PYRIGHT = $(SITE_PACKAGES)/pyright
+PLAYWRIGHT = $(SITE_PACKAGES)/playwright
+$(RUFF) $(PYTEST) $(COVERAGE) $(PYRIGHT) $(PLAYWRIGHT):
+	@$(MAKE) install-deps
+
+
+# -----------------
+# Helper packages not defined in `setup.cfg`
+# -----------------
+
+TRCLI = $(SITE_PACKAGES)/trcli
+$(TRCLI): $(UV)
+	@echo "-------- Installing trcli --------"
+	. $(PYBIN)/activate && \
+	  uv pip install trcli
+
+TWINE = $(SITE_PACKAGES)/twine
+$(TWINE): $(UV)
+	@echo "-------- Installing twine --------"
+	. $(PYBIN)/activate && \
+	  uv pip install twine
+
+RSCONNECT = $(SITE_PACKAGES)/rsconnect
+# Install the main version of rsconnect till pypi version supports shiny express
+$(RSCONNECT): $(UV)
+	@echo "-------- Installing rsconnect --------"
+	. $(PYBIN)/activate && \
+	  uv pip install "rsconnect-python @ git+https://github.com/rstudio/rsconnect-python.git"
+
+
+# -----------------
+# Type stubs
+# -----------------
+
+typings/appdirs: $(PYRIGHT)
+	@echo "-------- Creating stub for appdirs --------"
+	. $(PYBIN)/activate && \
+	  pyright --createstub appdirs
+typings/folium: $(PYRIGHT)
+	@echo "-------- Creating stub for folium --------"
+	. $(PYBIN)/activate && \
+	  pyright --createstub folium
+typings/uvicorn: $(PYRIGHT)
+	@echo "-------- Creating stub for uvicorn --------"
+	. $(PYBIN)/activate && \
+	  pyright --createstub uvicorn
+typings/seaborn: $(PYRIGHT)
+	@echo "-------- Creating stub for seaborn --------"
+	. $(PYBIN)/activate && \
+	  pyright --createstub seaborn
+
+typings/matplotlib/__init__.pyi: ## grab type stubs from GitHub
+	@echo "-------- Creating stub for matplotlib --------"
+	mkdir -p typings
+	git clone --depth 1 https://github.com/microsoft/python-type-stubs typings/python-type-stubs
+	mv typings/python-type-stubs/stubs/matplotlib typings/
+	rm -rf typings/python-type-stubs
+
+pyright-typings: typings/appdirs typings/folium typings/uvicorn typings/seaborn typings/matplotlib/__init__.pyi
+
+# -----------------
+# Install
+# -----------------
+## install the package to the active Python's site-packages
+# Note that instead of --force-reinstall, we uninstall and then install, because
+# --force-reinstall also reinstalls all deps. And if we also used --no-deps, then the
+# deps wouldn't be installed the first time.
+install: dist $(PIP) FORCE
+	. $(PYBIN)/activate && \
+	  pip uninstall -y shiny && \
+	  pip install dist/shiny*.whl
+
+install-deps: $(UV) FORCE ## install dependencies
+	. $(PYBIN)/activate && \
+	  uv pip install -e ".[dev,test]" --refresh
+
+install-ci: $(UV) FORCE ## install dependencies for CI
+	. $(PYBIN)/activate && \
+	  uv pip install -e ".[dev,test]" --refresh \
+	  "htmltools @ git+https://github.com/posit-dev/py-htmltools.git"
+
+# ## If caching is ever used, we could run:
+# install-deps: ## install latest dependencies
+# 	pip install --editable ".[dev,test]" --upgrade --upgrade-strategy eager
 
+# -----------------
+# Clean files
+# -----------------
 clean: clean-build clean-pyc clean-test ## remove all build, test, coverage and Python artifacts
 
 # Remove build artifacts
@@ -56,27 +195,10 @@ clean-test: FORCE
 	rm -fr .pytest_cache
 	rm -rf typings/
 
-typings/appdirs:
-	@echo "Creating appdirs stubs"
-	pyright --createstub appdirs
-typings/folium:
-	@echo "Creating folium stubs"
-	pyright --createstub folium
-typings/uvicorn:
-	@echo "Creating uvicorn stubs"
-	pyright --createstub uvicorn
-typings/seaborn:
-	@echo "Creating seaborn stubs"
-	pyright --createstub seaborn
-typings/matplotlib/__init__.pyi:
-	@echo "Creating matplotlib stubs"
-	mkdir -p typings
-	git clone --depth 1 https://github.com/microsoft/python-type-stubs typings/python-type-stubs
-	mv typings/python-type-stubs/stubs/matplotlib typings/
-	rm -rf typings/python-type-stubs
-
-pyright-typings: typings/appdirs typings/folium typings/uvicorn typings/seaborn typings/matplotlib/__init__.pyi
 
+# -----------------
+# Check lint, test, and format of code
+# -----------------
 check: check-format check-lint check-types check-tests  ## check code, style, types, and test (basic CI)
 check-fix: format check-lint check-types check-tests ## check and format code, style, types, and test
 check-format: check-black check-isort
@@ -84,22 +206,27 @@ check-lint: check-flake8
 check-types: check-pyright
 check-tests: check-pytest
 
-check-flake8: FORCE
+check-flake8: $(FLAKE8) FORCE
 	@echo "-------- Checking style with flake8 ---------"
-	flake8 --show-source .
-check-black: FORCE
+	. $(PYBIN)/activate && \
+	  flake8 --show-source .
+check-black: $(BLACK) FORCE
 	@echo "-------- Checking code with black -----------"
-	black --check .
-check-isort: FORCE
+	. $(PYBIN)/activate && \
+	  black --check .
+check-isort: $(ISORT) FORCE
 	@echo "-------- Sorting imports with isort ---------"
-	isort --check-only --diff .
-check-pyright: pyright-typings
+	. $(PYBIN)/activate && \
+	  isort --check-only --diff .
+check-pyright: $(PYRIGHT) pyright-typings
 	@echo "-------- Checking types with pyright --------"
-	pyright
-check-pytest: FORCE
+	. $(PYBIN)/activate && \
+	  pyright
+check-pytest: $(PYTEST) FORCE
 	@echo "-------- Running tests with pytest ----------"
-	python3 tests/pytest/asyncio_prevent.py
-	pytest
+	. $(PYBIN)/activate && \
+	  python tests/pytest/asyncio_prevent.py && \
+	  pytest
 
 # Check types with pyright
 pyright: check-types
@@ -115,15 +242,36 @@ format-isort: FORCE
 	@echo "-------- Sorting imports with isort --------"
 	isort .
 
-docs: FORCE ## docs: build docs with quartodoc
-	@echo "-------- Building docs with quartodoc ------"
-	@cd docs && make quartodoc
+# -----------------
+# Documentation
+# -----------------
+# Install docs deps; Used in `./docs/Makefile`
+install-docs: $(UV) FORCE
+	. $(PYBIN)/activate && \
+	  uv pip install -e ".[dev,test,doc]" \
+	  "htmltools @ git+https://github.com/posit-dev/py-htmltools.git" \
+	  "shinylive @ git+https://github.com/posit-dev/py-shinylive.git"
+
+docs: docs-serve FORCE ## docs: build and serve docs in browser
 
-docs-preview: FORCE ## docs: preview docs in browser
+docs-serve: $(PYBIN) FORCE ## docs: build and serve docs in browser
+	$(MAKE) docs-quartodoc
 	@echo "-------- Previewing docs in browser --------"
 	@cd docs && make serve
 
+docs-site: $(PYBIN) FORCE ## docs: build docs site
+	$(MAKE) docs-quartodoc
+	@echo "-------- Previewing docs in browser --------"
+	@cd docs && make site
+
+docs-quartodoc: $(PYBIN) FORCE ## docs: build quartodoc docs
+	$(MAKE) install-docs
+	@echo "-------- Building docs with quartodoc --------"
+	@cd docs && make quartodoc
 
+# -----------------
+# JS assets
+# -----------------
 install-npm: FORCE
 	$(if $(shell which npm), @echo -n, $(error Please install node.js and npm first. See https://nodejs.org/en/download/ for instructions.))
 js/node_modules: install-npm
@@ -142,65 +290,59 @@ clean-js: FORCE
 	@echo "-------- Removing js/node_modules ----------"
 	rm -rf js/node_modules
 
+
+# -----------------
+# Testing with playwright
+# -----------------
+
 # Default `SUB_FILE` to empty
 SUB_FILE:=
 PYTEST_BROWSERS:= --browser webkit --browser firefox --browser chromium
-install-playwright: FORCE
-	playwright install --with-deps
-
-install-trcli: FORCE
-	$(if $(shell which trcli), @echo -n, $(shell pip install trcli))
 
-# Installs the main version of rsconnect till pypi version supports shiny express
-install-rsconnect: FORCE
-	pip install git+https://github.com/rstudio/rsconnect-python.git#egg=rsconnect-python
+install-playwright: $(PLAYWRIGHT) FORCE
+	@echo "-------- Installing playwright browsers --------"
+	@. $(PYBIN)/activate && \
+	  playwright install --with-deps
 
-# end-to-end tests with playwright; (SUB_FILE="" within tests/playwright/shiny/)
-playwright-shiny: install-playwright
-	pytest tests/playwright/shiny/$(SUB_FILE) $(PYTEST_BROWSERS)
+playwright-shiny: install-playwright $(PYTEST) FORCE ## end-to-end tests with playwright; (SUB_FILE="" within tests/playwright/shiny/)
+	. $(PYBIN)/activate && \
+	  pytest tests/playwright/shiny/$(SUB_FILE) $(PYTEST_BROWSERS)
 
-# end-to-end tests on deployed apps with playwright; (SUB_FILE="" within tests/playwright/deploys/)
-playwright-deploys: install-playwright install-rsconnect
-	pytest tests/playwright/deploys/$(SUB_FILE) $(PYTEST_BROWSERS)
+playwright-deploys: install-playwright $(RSCONNECT) $(PYTEST) FORCE ## end-to-end tests on deployed apps with playwright; (SUB_FILE="" within tests/playwright/deploys/)
+	. $(PYBIN)/activate && \
+	  pytest tests/playwright/deploys/$(SUB_FILE) $(PYTEST_BROWSERS)
 
-# end-to-end tests on all py-shiny examples with playwright; (SUB_FILE="" within tests/playwright/examples/)
-playwright-examples: install-playwright
-	pytest tests/playwright/examples/$(SUB_FILE) $(PYTEST_BROWSERS)
+playwright-examples: install-playwright $(PYTEST) FORCE ## end-to-end tests on all py-shiny examples with playwright; (SUB_FILE="" within tests/playwright/examples/)
+	. $(PYBIN)/activate && \
+	  pytest tests/playwright/examples/$(SUB_FILE) $(PYTEST_BROWSERS)
 
-playwright-debug: install-playwright ## All end-to-end tests, chrome only, headed; (SUB_FILE="" within tests/playwright/)
-	pytest -c tests/playwright/playwright-pytest.ini tests/playwright/$(SUB_FILE)
+playwright-debug: install-playwright $(PYTEST) FORCE ## All end-to-end tests, chrome only, headed; (SUB_FILE="" within tests/playwright/)
+	. $(PYBIN)/activate && \
+	  pytest -c tests/playwright/playwright-pytest.ini tests/playwright/$(SUB_FILE)
 
-playwright-show-trace: ## Show trace of failed tests
+playwright-show-trace: FORCE ## Show trace of failed tests
 	npx playwright show-trace test-results/*/trace.zip
 
 # end-to-end tests with playwright and generate junit report
-testrail-junit: install-playwright install-trcli
-	pytest tests/playwright/shiny/$(SUB_FILE) --junitxml=report.xml $(PYTEST_BROWSERS)
-
-coverage: FORCE ## check combined code coverage (must run e2e last)
-	pytest --cov-report term-missing --cov=shiny tests/pytest/ tests/playwright/shiny/$(SUB_FILE) $(PYTEST_BROWSERS)
-	coverage html
-	$(BROWSER) htmlcov/index.html
-
-release: dist ## package and upload a release
-	twine upload dist/*
-
-dist: clean ## builds source and wheel package
-	python3 setup.py sdist
-	python3 setup.py bdist_wheel
+testrail-junit: install-playwright $(TRCLI) $(PYTEST) FORCE
+	. $(PYBIN)/activate && \
+	  pytest tests/playwright/shiny/$(SUB_FILE) --junitxml=report.xml $(PYTEST_BROWSERS)
+
+coverage: $(PYTEST) $(COVERAGE) FORCE ## check combined code coverage (must run e2e last)
+	. $(PYBIN)/activate && \
+	  pytest --cov-report term-missing --cov=shiny tests/pytest/ tests/playwright/shiny/$(SUB_FILE) $(PYTEST_BROWSERS) && \
+	  coverage html && \
+	  $(BROWSER) htmlcov/index.html
+
+# -----------------
+# Release
+# -----------------
+release: $(TWINE) dist FORCE ## package and upload a release
+	. $(PYBIN)/activate && \
+	  twine upload dist/*
+
+dist: clean $(PYTHON) FORCE ## builds source and wheel package
+	. $(PYBIN)/activate && \
+	  python setup.py sdist && \
+	  python setup.py bdist_wheel
 	ls -l dist
-
-## install the package to the active Python's site-packages
-# Note that instead of --force-reinstall, we uninstall and then install, because
-# --force-reinstall also reinstalls all deps. And if we also used --no-deps, then the
-# deps wouldn't be installed the first time.
-install: dist
-	pip uninstall -y shiny
-	python3 -m pip install dist/shiny*.whl
-
-install-deps: FORCE ## install dependencies
-	pip install -e ".[dev,test]" --upgrade
-
-# ## If caching is ever used, we could run:
-# install-deps: FORCE ## install latest dependencies
-# 	pip install --editable ".[dev,test]" --upgrade --upgrade-strategy eager
diff --git a/docs/Makefile b/docs/Makefile
index 72b14314c..ccd47dc8c 100644
--- a/docs/Makefile
+++ b/docs/Makefile
@@ -1,5 +1,6 @@
 .PHONY: help Makefile
 .DEFAULT_GOAL := help
+FORCE:
 
 define BROWSER_PYSCRIPT
 import os, webbrowser, sys
@@ -21,43 +22,40 @@ for line in sys.stdin:
 endef
 export PRINT_HELP_PYSCRIPT
 
-BROWSER := python -c "$$BROWSER_PYSCRIPT"
+BROWSER := $(PYTHON) -c "$$BROWSER_PYSCRIPT"
 
 # Use venv from parent
-VENV = ../venv
+VENV = ../.venv
+PARENT_PYBIN_TARGET=.venv/bin
 PYBIN = $(VENV)/bin
+PIP = $(PYBIN)/pip
+PYTHON = $(PYBIN)/python
+
 
 # Any targets that depend on $(VENV) or $(PYBIN) will cause the venv to be
 # created. To use the venv, python scripts should run with the prefix $(PYBIN),
 # as in `$(PYBIN)/pip`.
 $(VENV):
-	python3 -m venv $(VENV)
+	cd .. && $(MAKE) $(PARENT_PYBIN_TARGET)
 
 $(PYBIN): $(VENV)
 
 
-help:
-	@python -c "$$PRINT_HELP_PYSCRIPT" < $(MAKEFILE_LIST)
-
-dev-htmltools: $(PYBIN)  ## Install development version of htmltools
-	$(PYBIN)/pip install https://github.com/posit-dev/py-htmltools/tarball/main
-
-dev-shinylive: $(PYBIN)  ## Install development version of shinylive
-	$(PYBIN)/pip install https://github.com/posit-dev/py-shinylive/tarball/main
+help: FORCE
+	@python3 -c "$$PRINT_HELP_PYSCRIPT" < $(MAKEFILE_LIST)
 
-deps: $(PYBIN) dev-htmltools dev-shinylive ## Install build dependencies
-	$(PYBIN)/pip install pip --upgrade
-	$(PYBIN)/pip install -e ..[doc]
+deps: $(PYBIN) FORCE ## Install build dependencies
+	cd .. && $(MAKE) install-docs
 
 quartodoc: quartodoc_build_core quartodoc_build_express quartodoc_post ## Build quartodocs for express and core
 
 ## Build interlinks for API docs
-quartodoc_interlinks: $(PYBIN)
+quartodoc_interlinks: $(PYBIN) FORCE
 	. $(PYBIN)/activate \
 	  && quartodoc interlinks
 
 ## Build core API docs
-quartodoc_build_core: $(PYBIN) quartodoc_interlinks
+quartodoc_build_core: $(PYBIN) quartodoc_interlinks FORCE
 	$(eval export SHINY_ADD_EXAMPLES=true)
 	$(eval export IN_QUARTODOC=true)
 	$(eval export SHINY_MODE=core)
@@ -68,7 +66,7 @@ quartodoc_build_core: $(PYBIN) quartodoc_interlinks
 	  && echo "::endgroup::"
 
 ## Build express API docs
-quartodoc_build_express: $(PYBIN) quartodoc_interlinks
+quartodoc_build_express: $(PYBIN) quartodoc_interlinks FORCE
 	$(eval export SHINY_ADD_EXAMPLES=true)
 	$(eval export IN_QUARTODOC=true)
 	$(eval export SHINY_MODE=express)
@@ -79,17 +77,17 @@ quartodoc_build_express: $(PYBIN) quartodoc_interlinks
 	  && echo "::endgroup::"
 
 ## Clean up after quartodoc build
-quartodoc_post: $(PYBIN)
+quartodoc_post: $(PYBIN) FORCE
 	. $(PYBIN)/activate \
 	  && python _combine_objects_json.py
 
-site:  ## Build website
+site: $(PYBIN) FORCE ## Build website
 	. $(PYBIN)/activate \
 	  && quarto render
 
-serve:  ## Build website and serve
+serve: $(PYBIN) FORCE ## Build website and serve
 	. $(PYBIN)/activate \
 	  && quarto preview --port 8080
 
-clean:  ## Clean build artifacts
+clean: FORCE ## Clean build artifacts
 	rm -rf _inv api _site .quarto