Buying first bike, new or used?

I'm 17, almost 18. Looking to buy my first motorcycle. I'll be buying my first motorcycle, but I have ridden dirt bikes before, so I'm not a complete beginner.

When I turn 18, I plan on buying my first motorcycle, the question is, should I get a yamaha v star 250 (used beginner choice), or a 2017 honda rebel 300 abs new? I can get the yamaha for around $2200, and the honda for about $3700. I want a bike that will last me for 5 years when I buy it, probably with lots of riding done on it. (senior year of highschool and 4 years of college). I see people say that they are outgrowing the rebel too quickly and want a bigger bike, but I'm paying for my own insurance, so I don't want that to go up with a bigger bike, and I'd rather have a less powerful bike so I'm not tempted to speed as much.

So, with the price of gear and the MSF training course, what do you think I should do? I think the yamaha is a nice bike, but I'm not sure about buying used, as I don't know what it's been through and if it will last me 5 years. I do prefer the Honda more though, as it looks better, is new, slightly more powerful, and has abs brakes, which I think will really help since ill most likely be riding in all conditions.

So should I buy the yamaha with $2200, buy the honda with $2200 as a downpayment and loan the rest off, or wait a bit longer and pay the $3700 in full?

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