I’ve done a little bit of shopping around and you’ll be relieved to know that the Ninja 250R is not considered a sport bike with insurance companies. You’ll get a reasonable price, I believe. I’ve got some time on ya being 33 y/o but, I have never been licensed on a motorcycle and was quoted at around $600/year with full coverage by Progressive. That’s not bad, at all, I don’t think. Also, one of the best features I’ve noticed with the Ninja 250 and the 500 is their resale value. If you get either of these 2 and you decide in a year or 2 that you want something bigger you will not have a problem selling them. Knock around $500-$1000 off of the MSRP and it will get snagged up by somebody in your exact circumstance now that would rather spend a few hundred less and a few thousand miles on it than the full cost of a new bike. You’re doing yourself good with the 250, from what I’ve read, you won’t regret it.