I’m a few days late to this post but a few additional things to consider and some ramblings…

Whatever you’re looking at I’d run some insurance quotes. From my experience engine displacement and type of motorcycle are large factors in rates. I’d imagine there is a whole actuarial table for claims paid out on that combination that insurance companies use. As an example I could insure a 1200cc cruiser for half what a 600cc supersport cost even though they made comparable power(not power to weight figures though). I’ll also mention that my supersport insurance cost went down over the course of about 3 years of having no tickets/accidents to about half the original quote. It was not my first bike.

If you’re doing the maintenance, then in general, it’s easier on things without full fairings. Some bikes you don’t have to remove panels others you absolutely do just to do simple stuff like changing the oil. I own a ZX6R and oil changes are quick and simple with no panel removals. Coolant swaps require taking about 15 panels off and the removal of the entire nose of the bike just to see the radiator cap. It takes several hours. Another 950cc naked I own the radiator cap is right there. Just drain and fill. No tools required. Something to keep in mind when looking around.

You mentioned being particular on maintenance and motorcycles have shorter intervals than cars do for basically everything. As well as new maintenance items like chain cleaning, lubrication, and slack adjustment. If you follow the manual, some of those are as frequent as 400-600 miles. Most don’t actually do it that frequently but it’s certainly an item to keep an eye on. A dirty/dry chain can rob power and accelerate chain wear(chains are not particularly cheap). A lot of failures in a car that would be a non-event can put you in the hospital on a motorcycle. Fluid leaks? Annoyance in a car. Coating your rear tire in oil or coolant on a motorcycle can cause a crash as both fluids are super slick.

My first bike was a used CBR300R(286cc) which is really just a standard single cylinder motorcycle with a fairly upright seating position but is fully fared like a super sport. It was dirt cheap to insure and got around 75 mpg and you got to rev the pants off it. I really wish I had kept that bike. I sold it for nearly what I paid for it. There was only one time I felt the lack of power was problematic and that was a combination of about 3-4 other things all aligning at the same time in the worst ways. Everything else you just need to be diligent and plan ahead. A basic riders course should go over that at length.