Those were a lot of my wants when I was looking for my first bike earlier this year and I ended up finding a relatively high mileage, but fairly well maintained used Honda Shadow Aero 750. and it seems to check all of your needs.

Like you, I didn’t want to get something that will get me in trouble and I was initially a little hesitant about a 750cc bike, but this thing is heavy for the horses it puts out and entirely manageable and I’m already starting to “outgrow it”, especially on an interstate. Don’t feel intimidated by 650/750 cruisers, those are still great for beginners and you can actually go fast when you need to. Insurance is also reasonable here because it’s not a death speed demon that young 19 year old dipshits tend to get and then crash or get stolen. It’s a beautiful bike, but it’s not the coolest thing out there and that’s fine enough for me. I love the way it looks, it’s red and sticks out in traffic, it’s fun as hell to ride around on twisty New England back roads and I can still take it on the highway and do some longer distance trips on this thing.

As others said, Japanese is probably the way to go. Plenty of available parts, first party or third, they’re well engineered and put together, will last a long time if it was relatively well maintained and if you’re willing to learn you can start doing little bits of maintenance and repairs like I have.

I bought an official Honda service manual that has all the diagrams, specs and great pictures of how everything goes and troubleshooting steps, some tools, greases, etc and have already done some relatively minor maintenance and repairs and am doing some more in the next couple of days. At the same time, I’m also not frustrated at not being able to ride my bike because everything’s broken or wonky, and this is a 12 year old bike with a bunch of miles on it. Everything just works, save for a weird electrical issue I just encountered but am confident can fix.

Anecdotally, the guy who sold me this bike bought a nice, used Harley and immediately had to put money and time towards some crucial repairs that were not apparent at sale. Go figure.

I’m glad I went with the bike I went with, I still love it and will probably stick with it next year, but it has limitations that I’ve already encountered. Which is perfectly fine, I wanted a slower bike so I don’t wrap by dumb brains around a tree, but I will say the first time I rode it I was terrified and that went away quickly. Now I’m having a blast riding twisties, albeit relatively slowly, and sometimes even scrape a peg on a turn.

Don’t be scared of a 550lb 750cc cruiser, you’ll get used to it.