Frocco,
Hello. I rode a 2006 Stratoliner with 4000 miles before I bought my Fat Boy. I liked it and it had good power. I am only 5'8" and I fit that bike fine. It handled okay, but was not quite what I wanted. I waited and found my 2000 Fat Boy with 22000 miles. It had some nice add ons, including a Mikuni carb and Rinehart pipes. It was lowered about two inches and had beach bars on it. It fit me perfect, the old owner was only an inch taller. The power is about the same as the Stratoliner. I am sure the pipes and carb help. I truly believe the Fat Boy handles better, maybe because it is lower.
I know I am biased as I was only looking at the Stratoliner because my first Fat Boy deal went south. My brother has a bike shop and he had a great deal on this bike. I rode it for a day.
I then looked on Craigs list. There are some real deals on Harleys on there, at least in Md.
You may want to try to sell your bike first and then have cash to go buy what you want. I ended up paying $8800 for my Fat Boy with lots of extras and it looks brand new.
Anytime you are involving a dealer, you are not getting a great deal as I am sure you know. I never checked on Craigs List until someone else brought it up to me and I was amazed, much better prices than Ebay.
The best thing about owning a Harley is you don't have to explain anything to anyone. I know the Yamaha is a nice bike and may live a long time, but felt like I would always have to explain why I bought it instead of a Harley. I am not some kind of egomaniac who has to do what others think, but most people on this board will know what I am talking about. Most of us don't care what others think about what we ride. I don't care what others ride. It is just nice to pull up on my bike.
Anyway, ride whatever you are going to buy. I am sure if you like your bike, you can modify it a little to make it more comfortable. If you have to have a Harley, check out some used ones. You will find what I did. There are many out there that have already been modified for more than a fair price.
Just my .02. Good Luck!!
Ride Safe!
Eric