Well, I'm 53 and started riding again after parking my bike for my wife 19 years ago. And I'm loving it, and I live in a city with pretty bad traffic. I'm just loving it. I've always liked riding bikes MORE than driving any car. Even my '64 Alfa Romeo Spyder.
So. . . yeah, you can do it. You might like it. Especially if it isn't a bagger . . . I think with your past biking you'd just let the bagger park itself after a while. A Sportster, a Dyna, if you can handle the looks a Victory. . . I'm trying to buy American silly as it is, so I'd recommend those.
I know what you mean about working on the bikes. I was actually sort of happy I left my headlamp on and ran my battery down last month. It was fun to do just the simple task of taking the seat off, getting the battery out, recharging it, etc. And it made me do a few other things. I even looked at my '74 R90/6, parked in the back of the garage, not running since 1988. . . though I said "Nah."
I haven't had to do anything to the Fat Bob. I got it with an extended warranty that covers the first 30,000 miles services and nothing has gone wrong in a year and a half.