Sounds like the kind of "help" HD dealers are famous for. And I used to work for and was sponsored by a Harley dealer back in 51 & 52. Fifty years ago, all the Harley dealers I knew were great. I guess times and attitudes have changed.
I like the 1998 S3t the best, it had the thunderstorm motor and was the last year with a carb. 1999 and up were all injected and the FI system has some issues. Also think about getting a "t" model. the S3t came with matching painted hard bags.
You should also consider a Cyclone (M2), if you don't need the touring features of the S3T. No fuel injection issues (it's carburated), and it's actually quicker that the other models to about sixty...
I own a 2001 Cyclone - and I would tell you that reliability is not it's forte. Mine, at 25,000 miles, just had it's 25,000 mile service done, and by the time it is all done and finished, and after three visits..., it will have cost me $1500 to put this beast back on the road. The latest of problems was the bi-yearly broken motor mount which severed some oil lines, all of which had to be ordered, as Buell parts are seldom kept in stock, especially for the older ones, etc., etc. . If you are a mechanic, most of these are easy repairs, as nothing inside the engine has ever busted - but these bikes are weak electrically, and where the frame meets the engine. Good luck!
Do they have a more upright seating position like the S3T or a more race like position like a lightning?
The thing of it is I'm 6'2" 230lbs my wife is 6' 130 lbs.
I need a bike with a little room on it. That is why I'm looking at the S3 or S3T. Maybe the cyclone is just as big as the S3. I just have never seen one. My buddy has a white lightning (steel frame, don't know year) and I like riding his bike for a while but I can't get my wife and I on it.
The Cyclone riding position is more upright than the tube-framed Lightning, but not as upright as the S3T. Since it doesn't have a fairing (just a small but effective flyscreen), that's probably good. Leg room is excellent. For two-up, forget it.
Cyclone has a much more uprioght seating position. Especially mine, as I put the S3's handlebars on it! I am 5' 10" and 230 lbs., and it works for me, as far as the space. At your height, try it on for size first. As for Comfort, go to Corbin, and check out the saddles they have for the Cyclone. They even have one that you can have a backrest for the passenger seat, that can be removed, if desired. Very Comfortable. Very Wide, for a sportbike, for the pilot, and my girlfriend at 5' 10" never complains about the rear seat. I originally bought the cyclone because it's seat was much wider than other sportbikes... I am on my second saddle now and would not ride this bike without it. Good Luck!