Ryan,

Here are the details about using sudo with Vlad on Ubuntu

1) Add the following to deploy.rb
set :sudo_flags, sudo_flags << '-S'

2 ) Create askpass (~/bin/askpass)
#!/usr/bin/env ruby
puts gets.chomp!

3) Set permissions on askpass
sudo chmod 755 ~/bin/askpass

4) Add the following (or similar) to .bashrc (top of file)
if [ -z "$PS1" ]; then
    export SUDO_ASKPASS=$HOME/bin/askpass
fi

My website is in its infancy, but I wrote it up here:
http://nearapogee.com/posts

Thanks for everything. Hope this helps!