I'm looking to do the same, considering the following : rocker c, breakout, wide glide or another street bob. I love my 2011 street glide 103" very comfortable for long rides. I don't many trips over 500 miles plus, mainly ride around town and some 5 hour days out on the bike.
I do miss the wind some, and would like to just have something different than everyone else. Almost everywhere I go you see plenty of touring bikes, mainly street glides and for good reason too, its a great ride. Bought the street glide hoping my wife would have some interest in riding as well but she doesnt. I've had a street bob and loved it, kinda wish I didnt sell it. As of now I'm leaning towards the rocker c or breakout.

 

Where are you located.

 

Southwest Ohio area

 

Softail for sure! Throw air ride on it and your set to go from coast to coast. I'm not 70, 57 here but my body is starting to notice every bump in the road....until I adjust my suspension. Also, much like you the days of those long rides are a thing of the past. A Softail is so much easier around town, at least it is for me. I don't know that I would ever own anything again that wasn't a Softail unless I decide 100% to do an old shovel head project.

Since I have had this bike, 3 years now, I have had the chance too or I swap bikes with a buddy or two so they can check out the air ride. When I do, I can't wait to get off of their bikes and back on my own. I much prefer to sit "in" my bike rather than on my bike. Good luck Dude and keep us posted on your decision. It's always nice to watch and follow someones thought process and the end results.

EDIT: Of course in all honesty, I guess I would also have to say I am slightly biased too.