Some food for you thoughts....
I'm 63 and for my 60th, I got an 05 TBA. I had been looking at and lusting for an HD Wide Glide but was put off by the cost of even a 10 year old used one and it seemed that they were everywhere. Then I saw a TBA. So much for the HD's. Beautiful unique, classic lines, the sound, the size, etc. I couldn't be happier. Down side: there isn't as much aftermarket "stuff" as the HD's - Up side: There isn't as much aftermarket "stuff" as HD's to throw money at (forces you to be creative if you want something different on you bike to make it "your own".
More up-sides: easy handling, easy care and reliability, predictable throttle response (easy or "hot" - your choice.
Test ride - test ride - test ride, read the posts on this forum and magazine reviews, and make your own choice.
One last VERY IMPORTANT recommendation: get into a Motorcycle Rider Safety Course! It will be well worth it for you, now and in the future.
Good luck and have FUN!!