First off, this is primarily a Harley/Euro forum, so you're not going to get too many people telling you to get a Jap bike. Think of the audience here.
Now, I own a late model Sporty that I hardtailed and I just picked up an older Yamaha XS400 for $350 bucks, so I can see things from both sides. My Sporty is EFI, so I specifically wanted an older bike so I could learn about carbs and such. I yanked the Mikunis off, cleaned them up, replaced the slide gaskets, got new plugs/boots, verified the timing, etc and got her running. I basically spent ~100 in addition to the price of the bike. Granted, there are a few things I need to fix, but she runs and I've been riding her around a lot...for under $500 bucks...and this is from a guy who had never held a carburetor.
My advice...get a cheap Jap bike, ride around, get the rust off, save up while you're actually on the road riding, sell the Jap bike (can probably get all your money back, maybe even get more) buy a Harley. It might take you a month longer, but in the mean time you're riding. I'll be the first to admit that the sound of my Sporty gives me goodbumps, but that little XS is lots of fun to toss around.
Oh, when you are searching, try using Crazedlist.org. It's basically a Craigslist compiler and allows you to search multiple areas at once. Used it a lot when I was looking for the Yammy.
Now, I own a late model Sporty that I hardtailed and I just picked up an older Yamaha XS400 for $350 bucks, so I can see things from both sides. My Sporty is EFI, so I specifically wanted an older bike so I could learn about carbs and such. I yanked the Mikunis off, cleaned them up, replaced the slide gaskets, got new plugs/boots, verified the timing, etc and got her running. I basically spent ~100 in addition to the price of the bike. Granted, there are a few things I need to fix, but she runs and I've been riding her around a lot...for under $500 bucks...and this is from a guy who had never held a carburetor.
My advice...get a cheap Jap bike, ride around, get the rust off, save up while you're actually on the road riding, sell the Jap bike (can probably get all your money back, maybe even get more) buy a Harley. It might take you a month longer, but in the mean time you're riding. I'll be the first to admit that the sound of my Sporty gives me goodbumps, but that little XS is lots of fun to toss around.
Oh, when you are searching, try using Crazedlist.org. It's basically a Craigslist compiler and allows you to search multiple areas at once. Used it a lot when I was looking for the Yammy.