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Do you want an adventure bike or a cruiser? At some point your going to have to pick. Do you have your license yet? If not, I'd focus on that before getting too serious about buying a motorcycle. The class is a lot less expensive than a bike and you won't have to sell the bike at a loss because you decided riding is not your cup of tea, which is not uncommon after completing the riders course.

There's some merit to the idea that your objective when getting a motorcycle should be to become a better rider, not find your forever bike that's probably hard to find anyways. Swerving, negotiating curve, panic stops, etc will save rear on the road. I say a used dual sport 250/300cc that you can drop and no one will tell you it's worth half what you paid for it cause it's probably already been dropped many times, is a good first bike. You can take it off road to learn, which is much more forgiving than concrete or asphalt. You can likely tour on it if you're not expecting to go freeway speeds. Then when you're ready you can sell it, probably for close what you paid for it, and get the bike you want.

If you're willing to spend $6k, you can likely get a modern smaller bike that's few years old, but has FI and a shot at ABS, which is good for newbs. Something like a CB500x would be a light off road good mile eater. As bikes age parts can be at times harder to find and more expensive if you do. Sometimes there's Chinese parts too, so a lot will depend on the model too. If you see a nice looking older bike like you want there's a good chance it been sitting for an extended period at some point, which is not good for the bike, so that may add to the cost of the bike. I would say if you want an older bike that can do light off road and tour, the BMW F or G650GS might be worth a look. They're FI and gives you a shot at ABS. Looks they start at about $5k on CycleTrader. Good luck my friend and welcome.
 

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The Enfields seem like nice bikes, but I'd wonder about the service network. If you buy a Honda and something breaks. there's likely a dealer nearby, but perhaps not so with Enfield. I know when I had my Guzzi and I took it in for service, if the part had to come from Italy, it took at least a month to be delivered. That's aggravating here in the Frost Belt where the season is more limited.
 
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