Older Harleys
I disagree about money pit. I'd look for 88" TC if you can.
Also lets be honest you sound to busy to be going on cross country trips racking up massive miles.
https://flint.craigslist.org/mcy/d/o...975675653.html
You got a lot of votes for a EVO bike, and I love the EVO. If you can find a nice one in your price range it's a good choice and honestly they are becoming somewhat classic.
In the price range you want to stay in, you will no doubt come across early twin cams. The 88 inch TCs from late 90s early 2000 are really good bikes. Lots of good low mileage garage queens out there and, around here at least, $3500 - $5000 will get you a nice bike. The Softail models in particular seem to sell pretty reasonable. Lots of older Heritages and Fat Boys out there with low miles for good prices.
Things I would suggest you avoid on these early twin cams:
As others have said, try to avoid one with lots of mods for you first bike. Bolt on chrome stuff, pipes, air cleaners, and such are super common, so you will likely see that stuff, but serious engine work, big cams and stuff are probably better to pass on for the first bike. Overall general condition of the bike can tell you a lot. Don't pay any extra for the previously owners bolt on stuff. It doesn't make the bike worth any more no matter how much they spent on the stuff. If it is fuel injected and has pipes and a high flow air cleaner, it should have a fuel tuner to prevent it from running lean.
Before 2000 I would avoid fuel injection. The old MMI injections were very good for the most part and are expensive and hard to support. Carbs are a better choice. I have had 2 with the Delphi fuel injection systems and they have been excellent.
The early TC engine had pretty poor tensioner system for the timing chains. You can read for days on these forums about what to do about them, what upgrades are available. Study up on this stuff before you start looking seriously. Remember to take a lot of stuff you read with a grain of salt. There are people who hate everything.
Do some reading and research by reading on here and ask questions if you don't understand something.
Good luck with the search and have fun








