wow, jealous, I would love a bike, some day when I'm not poor I want a Harley, I would really love a vintage 1950s style one.
I hope you find people to ride with!
believe it or not Harleys are more affordable than you think, financing makes this possible. Granted I bit off a little more than I could chew by going brand new on a pricier model with a "few" customizations, so I'll be paying for the next few years.
Depending on your size (im a larger guy, meaning larger bike, meaning larger price tag) you can get a 2010 883 Sportster for $7000, at $0 down, thats less than $120 a month over 5 years (@9.49%, motorcycles are considered recreational vehicles, thus higher loan rates).
Used is always a good way to go, especially with Harley, hating to knock on the other makes out there, but how many older model honda/kawasaki/yamaha cruiser bikes do you see on the road compared to older Harleys.
Models haven't switched much over the the decades so finding replacement parts is much easier down the road compared to other Makes when the same model of a bike changes drastically every year.
You said that you were looking for a vintage 1950's look, they just came out with the Sportster '48, it is a sharp looking ride, base model goes for $10,500
http://www.harley-davidson.com/en_US/Content/Pages/2010_Motorcycles/2010_motorcycles.html?locale=en_US&bmLocale=en_US#/model/xl1200x
I gotta admit though, the dealership near me loves me because I've now had that bike for 7 months, and since then, I've had 8 people that I work with and friends buy bikes. Extended exposure to motorcycles increases the desire to purchase, realization of affordability severely increases this
