I paid the "price of admission" to the "Harley lifestyle" with my 2012 Harley Road Glide Ultra without the benefit of wasting even more money on a smaller Harley to get onto the "bigger" Harley's. It was a very expensive lesson...if Triumph would have come out with the 2013 red/black combo R3T before June of 2012 I would have passed on even owning a Harley. But I learned my lesson...if you want to spend a lot of money on a motorcycle that has minimal performance with a great paint job and a lot of accessory availability then Harley may be your bike. Having lost over $20,000 roughly on the "privilege" of entering the Harley lifestyle...it just wasn't worth it. It was a "nice" bike just not worth the money I ended up spending on it and ended up being a lesson well learned. Now if I had a ton of money and was collecting a number of bikes to ride on...I could fit a Harley into the mix but other manufacturers bikes would come first (a Roadster and another 1700 Thunderbird, Gold Wing come to mind) and then I'd see what Harley might have to offer but it probably wouldn't be ridden very much.
Dennis