I'd agree with you on the Sportster - I may be biased as I have one!
I went from an airhead to a 2006, last of the carb 883 and haven't regretted it. Easy maintenance: single carb, hydraulic valves and belt drive with bags of character. Fast enough for me and limitless accessories available!
The biggest pain if you have spoke wheels with inner tubes is a roadside puncture, but I'm not sure I'd be bothered to try and remove the wheel at the roadside even if I had a centre stand.
There are plenty of lifts available for use at home once you get towed!