2006 Suzuki GZ250. Bought at 3100 miles and I've already gotten it up to 3750. I've been wanting a motorcycle for ages, and I knew better to not start on something too powerful. It's so fun to ride! And comfortable, too, unless I'm on it for 3+ hours, which I do without even knowing because of how fun it is.
Although there is an itch to get something more powerful now. I won't be able to afford the insurance on that though lol. To get that feeling, I test rode a Harley Davidson Sportster 48, not what people think of a "fast" motorcycle but it might as well be a rocket ship compared to what I have. But I'm super happy with my GZ250 and will keep it through at least April 2024.
I started on a naked 300 and got a sport tourer 800 just 5 months later. I had the luxury of keeping the 300 and when I came back to it the following spring, I couldn't beleive how much fun it was. It's still my commuter because the 800 is a bore in traffic and <50mph and I can feel the extra 150lbs. I'm sure a recent 650 to 900 naked would be better, but there's nothing wrong with the 300 for its role. Most complaints stem from rider inexperience (making a big deal about wind) and from comparing performance to motorcycles only rather than all motor vehicles around you. My only fundamental complaint: bar and seat vibration at highway speeds/7,000rpm+ (reference: redline is 10.5k, 70mph is 7700rpm). And for that, I'm always considering a larger commuter but still haven't gotten around to it