diff --git a/Makefile b/Makefile
index a3f53b7c..bd69dfbc 100644
--- a/Makefile
+++ b/Makefile
@@ -1,11 +1,12 @@
 .PHONY: test
 
+GNU_SED := $(shell command -v gsed || command -v sed)
 now := `date '+%Y-%m-%d_%H%M'`
 
-installer:
+installer: thinkdifferent
 	@echo -n "Building unified install script... "
 	@cat build/installer/main.sh build/installer/_*.sh | \
-		sed -e '1,30s/echo "\(\s\+\[\)/echo "        \1/' \
+		$(GNU_SED) -e '1,30s/echo "\(\s\+\[\)/echo "        \1/' \
 			-e '1,20{/^# shellcheck source=_.*$$/,+1d}' \
 			-e '/^main "$$@"$$/{H;d};$${p;x;s/^\n//}' \
 			-e 's^main\.sh^bash ./setup.sh^' \
@@ -13,6 +14,35 @@ installer:
 		> setup.sh
 	@chmod +x setup.sh && echo "Done!"
 
+dev-env:
+	@echo "Go stick the kettle on, this'll take a while." && sleep 2
+	@echo
+	@echo "[1/5] Destroying Vagrant VM and purging package caches..." && \
+		rm -rf ./composer ./node_modules ./vendor; vagrant destroy -f
+	@echo
+	@echo "[2/5] Installing Composer/NPM packages and building assets..."
+ifeq (, $(shell command -v composer))
+	@echo "Composer not available, package installation will run in Vagrant instead."
+else
+	@composer install --no-interaction --no-progress --no-suggest || true
+endif
+	@npm ci && npm run dev
+	@echo
+	@echo "[3/5] Creating the new VM..." && \
+		vagrant up --no-provision || true
+	@echo
+	@echo "[4/5] Creating the 'servidor' user..." && \
+		vagrant provision --provision-with=user
+	@echo
+	@echo "[5/5] Restarting Vagrant VM to run installer..." && \
+		make installer && vagrant reload --provision-with=installer
+
+thinkdifferent:
+ifeq (Darwin,$(shell uname)$(shell command -v gsed))
+	@echo "To build the installer on OSX, you must first brew install gnu-sed"
+	@exit 1
+endif
+
 test:
 	@vagrant ssh -c "cd /var/servidor && sudo -u www-data phpdbg -qrr vendor/bin/phpunit -c build/phpunit/config.xml"
 
diff --git a/README.md b/README.md
index a0b96002..986d7209 100644
--- a/README.md
+++ b/README.md
@@ -12,8 +12,9 @@ Servidor is still very much a work in progress, but what has been [added so far]
 ## Table of Contents
 
 * [Introduction]
-* [Table of Contents]
 * [Installation]
+  * [Interactive Setup]
+  * [Startup Script]
 * [Development]
   * [Running Tests]
 * [Contributing]
@@ -26,7 +27,10 @@ you also have the ability to manually trigger a `git pull` on any given project
 
 ## Installation
 
-> **WARNING!** Servidor is not yet ready for production use!
+> **NOTE: Servidor is still a work-in-progress!**  
+> As such, there are some parts that likely aren't as secure as they could be, so  
+> **exercise appropriate caution if you intend to use it on a public-facing server!**  
+> If you find anything that can be improved, PRs are open and greatly appreciated.
 
 #### Interactive Setup
 
@@ -59,27 +63,18 @@ curl -s https://raw.githubusercontent.com/dshoreman/servidor/installer/setup.sh
 
 ## Development
 
-Servidor is setup to use Vagrant for development. To get started, first clone the repository and run `vagrant up`.  
-
-Installation happens automatically as part of the provisioning process, but the installer will not build frontend assets if it
-detects Vagrant. Instead, you'll need to install and build them separately after running `vagrant up`:
+To get started, run `make dev-env` in the project root. Servidor relies on [Vagrant] for development, so this command  
+takes care of creating the VM, running the necessary prep, and installation of Servidor within the dev environment.  
+After the initial setup, standard Vagrant commands can be used to `up`, `suspend`, `reload` and so on.
 
 ```sh
-# Clean-install NPM packages from the lock file
-npm ci
-
-# Compile the frontend assets for development
-npm run dev
+# tl;dr:
+git clone https://github.com/dshoreman/servidor.git
+cd servidor && make dev-env
 ```
 
-Alternatively, you can use `npm run watch` or `npm run hot` to have assets automatically rebuilt during development.
-
-By default, Servidor can be accessed at http://servidor.local:8042. If you have [vagrant-hostsupdater] or similar, this will be
-mapped automatically. Alternatively you can use http://192.168.10.100:8042, or run the following to update /etc/hosts:
-
-```sh
-echo '192.168.10.100 servidor.local' | sudo tee -a /etc/hosts
-```
+Due to memory constraints within the VM, static assets are initially built during `make dev-env`.  
+To recompile assets automatically when you make changes, run `npm run hot` or `npm run watch`.
 
 ### Running Tests
 
@@ -90,15 +85,20 @@ Other make commands are available such as `make syntax` to run other CI tools. F
 
 ## Contributing
 
-As noted above, Servidor is still very young. Your ideas, code and overall feedback are all highly valued, so please feel free to
-open an issue or pull request - the latter should go to the develop branch. Thanks! :heart:
+Where possible, issues are grouped into one of various projects based on the page/section they apply to, so if you want to
+find something to work on in a certain part of Servidor, then the Projects tab is a good place to start. Questions, bug reports,
+ideas and PRs are all welcome and highly appreciated, so don't be afraid to ask if there's something you're not sure of!
+
+If you use IRC, find me in *#servidor* on Freenode where I'll be happy to answer questions in a more real-time fashion.
 
 [Introduction]: #servidor
-[Table of Contents]: #table-of-contents
 [What it Does]: #what-it-does
 [added so far]: #what-it-does
 [Installation]: #installation
+[Interactive Setup]: #interactive-setup
+[Startup Script]: #startup-script
 [Development]: #development
 [Running Tests]: #running-tests
 [Contributing]: #contributing
+[Vagrant]: https://vagrantup.com
 [vagrant-hostsupdater]: https://github.com/agiledivider/vagrant-hostsupdater#installation
diff --git a/Vagrantfile b/Vagrantfile
index 58ef6af0..03087168 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -9,27 +9,39 @@ Vagrant.configure("2") do |config|
   config.vm.network "private_network",
     ip: "192.168.10.100"
 
+  config.vm.provider "virtualbox" do |vb|
+    vb.name = "servidor-dev"
+    vb.linked_clone = true
+    vb.memory = "1024"
+  end
+
+  config.vm.provision "user", type: "shell", run: "never" do |s|
+    s.inline = "useradd -b /var -UG www-data -s /usr/sbin/nologin --system servidor && echo 'User added!'"
+  end
+
+  config.vm.provision "installer",
+    path: "setup.sh", args: "-v",
+    type: "shell", run: "never"
+
   config.vm.synced_folder ".", "/vagrant",
     disabled: true
 
   config.vm.synced_folder ".", "/var/servidor",
-    create: true, owner: "998", group: "998",
+    create: true, owner: "servidor", group: "servidor",
     mount_options: ["dmode=775,fmode=664"]
 
-  config.vm.synced_folder "./resources/test-skel", "/var/servidor/resources/test-skel",
+  config.vm.synced_folder "./storage", "/var/servidor/storage",
+    create: false, owner: "servidor", group: "www-data",
+    mount_options: ["dmode=770,fmode=660"]
+
+  config.vm.synced_folder "./resources/test-skel",
+    "/var/servidor/resources/test-skel",
     create: false, owner: "www-data", group: "www-data",
     mount_options: ["dmode=775,fmode=664"]
 
-  config.vm.synced_folder "./resources/test-skel/protected", "/var/servidor/resources/test-skel/protected",
+  config.vm.synced_folder "./resources/test-skel/protected",
+    "/var/servidor/resources/test-skel/protected",
     create: false, owner: "vagrant", group: "vagrant",
     mount_options: ["dmode=775,fmode=600"]
 
-  config.vm.provider "virtualbox" do |vb|
-    vb.name = "servidor-dev"
-    vb.linked_clone = true
-    vb.memory = "1024"
-  end
-
-  config.vm.provision :shell, path: "setup.sh", args: "-v"
-
 end
diff --git a/build/installer/_install.sh b/build/installer/_install.sh
index eabb6550..de8a6e1a 100644
--- a/build/installer/_install.sh
+++ b/build/installer/_install.sh
@@ -14,10 +14,12 @@ install_servidor() {
 }
 
 prepare_home() {
-    log " Creating servidor system user..."
-    useradd -b /var -UG www-data -s /usr/sbin/nologin --system servidor
     if ! is_vagrant; then
+        log "Creating servidor system user..."
+        useradd -b /var -UG www-data -s /usr/sbin/nologin --system servidor
         mkdir /var/servidor && chown servidor:servidor /var/servidor
+    else
+        log "Skipped system user creation - when running in Vagrant, this is done by make dev-env."
     fi
 
     log "Adding www-data to the servidor group..."
@@ -25,13 +27,14 @@ prepare_home() {
 }
 
 clone_and_install() {
-    cd /var/servidor || (err "Could not create system user!"; exit 1)
+    cd /var/servidor || (err "Home directory for servidor was not created!"; exit 1)
+
     if ! is_vagrant; then
         sudo -u servidor git clone -qb "${branch}" https://github.com/dshoreman/servidor.git .
     fi
 
     log "Installing required Composer packages..."
-    is_vagrant && c_dev="" || c_dev="--no-dev"
+    is_vagrant && c_dev="--prefer-source" || c_dev="--no-dev"
     sudo -Hu servidor composer install ${c_dev} --no-interaction --no-progress --no-suggest
 
     log "Compiling static assets..."
diff --git a/setup.sh b/setup.sh
index 0236e269..ee80f303 100755
--- a/setup.sh
+++ b/setup.sh
@@ -81,21 +81,23 @@ install_servidor() {
     finalise && print_success
 }
 prepare_home() {
-    log " Creating servidor system user..."
-    useradd -b /var -UG www-data -s /usr/sbin/nologin --system servidor
     if ! is_vagrant; then
+        log "Creating servidor system user..."
+        useradd -b /var -UG www-data -s /usr/sbin/nologin --system servidor
         mkdir /var/servidor && chown servidor:servidor /var/servidor
+    else
+        log "Skipped system user creation - when running in Vagrant, this is done by make dev-env."
     fi
     log "Adding www-data to the servidor group..."
     usermod -aG servidor www-data
 }
 clone_and_install() {
-    cd /var/servidor || (err "Could not create system user!"; exit 1)
+    cd /var/servidor || (err "Home directory for servidor was not created!"; exit 1)
     if ! is_vagrant; then
         sudo -u servidor git clone -qb "${branch}" https://github.com/dshoreman/servidor.git .
     fi
     log "Installing required Composer packages..."
-    is_vagrant && c_dev="" || c_dev="--no-dev"
+    is_vagrant && c_dev="--prefer-source" || c_dev="--no-dev"
     sudo -Hu servidor composer install ${c_dev} --no-interaction --no-progress --no-suggest
     log "Compiling static assets..."
     if is_vagrant; then