I have _only_ 1 production application hosted on a hand-built DigitalOcean stack - hell it was a such a process I wrote a guide on how to do it, mainly for my own benefit in the future.
http://tech.pro/tutorial/1335/devops-for-dummies-vps-configu...
Surprise surprise, I try to follow _my own guide_ on a new project I started and it doesn't work as expected. Either RVM changed since writing it, Ubuntu issue with locales preventing postgres from starting, or the odd issue with postgres not installing with a default user. It's a cluster.
Alright, enough fiddling about. I bought myself a book to learn from a professional [0]. Surprise surprise! Outdated not 1 month after it's been released. No longer working, again hunting down the comments area. :P
There's a reason why Heroku is so popular: it makes deployments mind-numbingly simple. (Plus you can scale, but let's worry about that after the app actually runs!)
I'm going to give this a shot using a brand new Ubuntu 13.10 x64 DigitalOcean VPS with a simple CRUD rails application I have. But I'd bet my left arm that something is going to go wrong and yet again I'll have to dive deep into the recesses of the web.