I've never owned an HD FL. Mine (still) is a 97 FXD. I rode out to the 95th with a friend of mine who had a first year HD FI motor. IIRC it was a new 1998 Evo Ultra Classic. He was the HOG Chapter Director, so he always got best. An unusual feature, again iirc, was that it did not have a low fuel indicator lamp. I vividly remember getting off the interstate in Mackinaw City during the "Ride Home" to Milwaukee and he coasted, ouf of gas, right up to a fuel pump at a service station.
I think there were some problems with the rear cylinder getting hot on some of the earlier twin cams. As in glowing red.
In my expereince, I've not heard many complaints about the Ultra being underpowered or having too many problems, including Evo's. A low mileage Evo would give you plenty of miles of fun and be simple to maintain.
My $.02