Rebuilt is salvage and salvage is a pox. Resale will be a pain at best. Make sure you're getting a hell of a deal.
The more I see on this thread the more I think "neither".
Unless there is a real reliability reason to not get a V-rod, I guess I don't understand the dislike there. 30 k miles on a mid-displacement, liquid cooled V-twin isn't bad, and based on the model year amounts to 3000 miles or so per year.
I did check with my insurance company a bit ago. They would do liability only on the rebuilt Dyna. The price is not quite good enough for me to go without full coverage, so that one is out unless I can talk him into about half what he's asking. I'm not a big enough D-bag to do that. I did find out that I think I like the dyna platform at least so there's that.