I use Capistrano and am quite happy with it, but even if you don't go that way, seriously look into some kind of deployment management software. Versioned deplo

I use Capistrano and am quite happy with it, but even if you don't go that way, seriously look into some kind of deployment management software. Versioned deployments, simple and automatic rollbacks if something fails, and the ability to easy scale up deployments if you wind up breaking out into multiple servers for app/db/web. It turns updating your server from a mild headache to one line that you actually enjoy typing in.