In general i definitely recommend buying used. For those criteria specifically I’d recommend looking for a used Honda Rebel.

If you’re open to naked sport bikes with a more upright riding position you could look at cb300, z300, mt-03 which should have pretty reasonable insurance rates as well.

Also kind of depends on your size as well in my opinion, if you’re 6’6 320 a 300cc may feel a bit anemic even as a beginner. Regardless I’d recommend erring on the side of smaller displacement for your first bike. While it’s true that at the end of the day it does all come down to throttle control, a smaller cc bike will provide a wider margin of error as well as being lighter and more maneuverable.

Like everyone stated, buy used, and probably stick to one of the popular Japanese brands (Kawasaki, Suzuki, Honda, Yamaha). Parts are plentiful and are all going to be about the same price between brands.

When you find a potential bike you like, do a quick Google search to see if there were any major mechanical issues or recalls with it.

If this is your first bike, BE CAREFUL out there and take everything slow. Definitely take the MSF course - it’s actually great fun and you’ll learn a lot.

Good luck!

Get something second hand so if/when you drop it, it’s not an issue.

Honda or Kawasaki is a good place to start.

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Im an Enduro rider but i had some of the same challenges as you when I chose to start riding again after 20 years.

• look at what dealerships sell in your area. A friend of mine bought a moto guzzi and it was a fantastic bike but only one dealership existed in a very large territory that offered parts. Whatever brands local dealership sells will proportionally indicate part availability.

• maintenance for most motorcycles can be broken down to similair components. Fortnine has a video on tearing apart and putting back together a motorcycle and a general indication of the fundamental components to expect to deal with. As fancy as a bike is, there’s ultimately a finite amount of things you will deal with. Also if you can find it, grab yourself a physical copy of a repair manual. It’s nice to have for even dumb little things.

• depending on your maturity, I would consider something between 500-700cc. Most people I know who have bought a sub 500cc bike end up selling it again at a loss in a very short period of time. I ended up buying an 800cc as my first bike. I took riders training again, and had several years of driving under my belt. I dont have a need for speed and ive never had an issue with being unable to control my bike. But if you decide to go on a highway with your bike, having the jam to speed out of a sketchy situation becomes another tool in your kit.

I really like fortnine’s videos when it comes to perspective on bikes, and gear. I watch a lot of videos regardless of how long I’ve been riding. Here’s one on beginner bikes.

https://youtu.be/ifBNDeMZQkI

If you want to do new maybe look at Ryal Enfield. The Interceptor 650 is a standard motorcycle which seems pretty good. They also have a Meteor 350 cruiser and the super meteor 650 cruiser. I have no personal experience on any but I’ve read and seen good things. They also gave a 3year factory warranty with unlimited miles.