After a several month hiatus (filled with such activities as getting married and honeymooning), I'm finally getting back into the swing of "normal" life.
I've been working on a pet project using Sinatra and Unicorn (doing some long-polling stuff, so I needed to support multiple connections even in dev). Unfortunately, this combination makes code reloading tricky to tackle, as it rules out shotgun entirely, and seems to also bust Sinatra::Reloader.
After a couple hours of HUPping unicorns manually, I decided that I needed a more robust solution. Some digging led me to the FSSM gem by ttilley. This library will watch your file system for events and runs a registered callback when they occur. A few minutes of hacking and my reloading woes are solved!