If you believed the Easy Rider dream you likely saved your dollars over the years and bought yourself a hog.
Dennis Hopper should have been paid in Harley Davidson stock for the cultural influence and the sales that he generated thanks to his motorcycle riding magic in the movie. Hopper not only starred in the movie but he also directed and co-wrote the film so really in the modern day product placement movie madness Hopper would have made bank with this movie.
So the biggest problem is the cost of this American icons. You really need to research Harley Davidson motorcycle prices before you make any purchase decisions.
The cost associated with making a new purchase is not to be taken lightly. I mean in some parts of the USA you can buy a nice piece of land for about the same price.
All the magazine articles that you see are usually suggested retail prices. Those can be vastly out of sync with reality in some situations. Even than some dealers will stick to Harley Davidson motorcycle prices that come from head office but they might throw in some freebies that actually make the purchase price lower.