Check with me in a couple weeks. I just did this exact thing, not that I dislike sport bikes and I will have another in the future but I've wanted a Harley bagger for a little while and came across one that appealed to me so I'll give it a try and see how it goes.
If you like the Softail heritage give a look to the Road King Classic. That's what I ended up with and I'm not a huge fan of Road Kings in general appearance wise BUT the wire wheels, white wall tires and leather bags all jumped out at me and I really really like the look of the bike. My understanding is the touring bikes ride better then the softails pretty much everywhere including in town.
Ive ridden it twice for a total of about 30km's so I only really have initial impressions. Once at a walking pace you don't notice the weight, the bike is well balanced and very manouverable relatively speaking. I didn't get this same impression of a couple Japanese cruisers I rode a year or so back, I really felt the weight on those and to be honest couldn't get very comfortable with them. Power is fine, expected a dog but short shift it and the torque pulls you along very well. Yes it vibrates at an idle but really it's kind of cool and not like the jack hammer my KTM LC4 was. Smoothes out right away and you have a slight "thump" as you cruise along that is actually kind of peaceful, I wouldn't want it any smoother personally.
Thats all I got right now in terms of how they ride due to my short couple of trips. I feel like I'm probably going to enjoy it and next year jump in with both feet and buy a newer Road Glide as that's the bike I really like in the line up.
I'd make sure to get one with the newer fuel injection (I think 02 and newer) and if your looking at a bike with a higher mileage 88" engine you'll either want to find out if the cam chain tensioners are done or count on doing them at some point. Otherwise all my research has shown them to be very reliable but that isn't a first hand experience.
For what it's worth I do still have a supermoto for some stupidity. I'm not 100% sure I could live with just a Harley but with that said I can't have my supermoto as an only bike either. Opposite ends of the motorcycle world the two bikes I have but I expect it to work for me.
Oh one last thing. Coming off performance bikes, bags are about the coolest thing in the world. Instead of ramming my pockets with junk everything goes in the bags and I just ride on. Good luck on the search.