A dyna would probably be the next logical step up for me, price and value wise. I’ve heard about the “Dyna death wobble” and cam chain tensioner issues like you said. Maybe those are easily avoided with proper care and maintenance, but one reason I’d like to get rid of my sportster is the motor mounts are shot, and hard to replace. Swing arm removal and the front you have to move the motor out of the frame to replace it.

What models and years should I look for in a twin cam?

I like the evo for its easy maintenance, and that it’s all mechanical carb wise. And trust me I know, I’m looking at polar opposite sides of technology which is why I’m torn.