I started with Leather Neck Jim's throw-overs on my Dyna, but they were a PIA and behaved as above. These bags are good sized for a Dyna and reasonably priced for quality leather.
Added the Easy Brackets, relocated the tail lights and cut off the yoke:

 

Throw overs are ok if you want to have those ugly brackets on the bike all the time. You can protect the paint with some of that clear plastic sheeting stuff. They are cheaper, but your stuff will get wet.

I would use a T bag system. Get to where you're going, take the bag off, and there you are.