I've read about people having problems with the Droid deleting emails and SMS messages. I've never had this problem. Sure it deletes my SMS messages when they go over the limit that I specified (100 instead of the default 200), but never has it deleted anything I didn't ask it to. I haven't heard of this happening a lot and it's really hard to tell if it's a pebcak error or simply a defective device.
As for only syncing with USB....why? What is the point of getting such an advanced device and going back to the 90's with it. Sure you can use the browser and use apps and such, but isn't that just as much of a 'security' issue? And to be honest, if your company is supporting ActiveSync and has Outlook Web Access enabled, EVERYONES Outlook mail in your company is technically "on the web". As long as your ActiveSync is properly configured and is secured with SSL, then you're just as secure as you normally would be. People have already found a way to do a man in the middle attack with SSL, is that going to completely stop you from using the internet. Probably not. If you're concerned about your info being saved in the google cloud then don't check off the setting on the Droid to backup your settings and such to Google.
As for the WinMo 5.0 reghack. Yeah I knew about it. I just didn't think it was worth applying it to a 3 year old phone with a battery that was so dead it would only last me 2 minutes talk time and half a day if I used it to SMS. Even when the battery was in its prime, I got so much email through work that once I hooked it up to ActiveSync the phone only lasted about 6 hours before it needed a charge.