For that kind of money I'd consider looking at a newer used Japanese bike, either 2 cylinder or 4 cylinder. The Japanese bikes depreciate much faster than Harleys because of Harley's excellent marketing, similar to John Deere's marketing.
I like older Suzukies, a 1980's GS1100 4 cyl runs $800 to $1500 depending on the time of year. Add $250 to overhaul the carbs, another $250 for new tires and change the brake fluid and you have a very nice bike. They are lighter, faster, quieter and more comfortable than the Harleys I've test driven and they cost less than half as much as a similar Harley.
Your opinions may be much different depending on what you are looking for. I'm one of the few people who likes American cars, American pickups and Japanese mototcycles. Other people always tell me they are the worst of both worlds.
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Today's Featured Article - Talk of the Town: The Saga of Grandpa's Tractor - by The following saga is from the Tractor Talk Discussion Forum. Someone. The saga starts with the following message: Hey guys I have a decision to make. I know what you all will probably suggest and it will probably agree with me way down inside, but here it is. I have a picture blown up and framed in my "tractor room" of a Farmall M. It was my Grandpa's tractor, of which whom I never got to meet. He froze to death getting this tractor out of the barn to pull a truck out of the ditch before I was born. Anyway my dad and aunt had to sell it at the auction,
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