I think this question would be more appropiate in http://stackoverflow.com than here. Your doubts are pretty technical for the scope of this community.
" For example, instead of saying your position was for a guild in EVE, state that it was a leadership role in a 2500+ strong online community. Emphasize the elements of the position that directly relate to the skills that a prospective employer would hire you for"
Even though your in-game experience could really have been helpful to your work skills, I think putting this in your resume might backfire, PR departments wouldn't take this seriously.
I'm just starting with Rails and I've found Heroku the easiest Rails hosting provider. They don't give you a shared server machine, you upload your application directly, and there's even a free usage tier if your app is low-traffic.
Using git, you just push the app to Heroku with your credentials and you're set.
Also, you can upgrade or downgrade the maximum performance as needed by the spikes of traffic so you never pay for more that you use.
If so, I've become very confortable with LastPass. There are even a lot of passwords I don't really know as they were automatically generated and are automatically filled-in
Reminds me of this comic: http://xkcd.com/927/