If you wanted to stay with the Star line, I owned a 2001 V-Star 1100 that I really enjoyed and two coworkers love their V-Star 650s. I went from a Suzuki S40/Boulevard 650 to it, which may sound like a big jump from your V-Star 250 but believe me, it's not once you spend a week with a 650 or 1100 because their weight is carried so low. On the plus side, the 1100 in particular has all the low-end grunt you'd ever need and it sounds pretty good too. I put on a Mustang seat and passenger backrest, and the two of us were all-day comfortable. I also had a touring windscreen and wind guard "lowers" that eliminated helmet buffeting and seemed to strike the perfect balance between airflow and chill protection. I think I got about 37 mpg; a little higher on country roads. Easy to work on, reliable engine and shaft drive. I also put on a mustache bar with integrated highway pegs and a few other mods that made it cozy for long days. On the minus side it is big and hot for city summer riding. Those jugs are right between your legs and you'll bake if you get stuck in traffic in the peak of summer. In the winter, it's free torso heat, but in the summer you may find yourself wanting a smaller, lighter and more maneuverable bike for shorter trips. It's also a style more suited to bombing through country roads and highways, not tight-and-twisty corners and certainly not off-road conditions (though it'll handle gravel and flat dirt just fine as long as the short suspension doesn't bottom out). If that suits your riding style, then perfect, but if you start wanting to take turns tighter and faster, it doesn't take much to scrape the pegs. Something to consider anyway. You can get a used V-Star 650 or 1100 in good condition, well-equipped for $3k-4k all day long. They're so damned reliable, I don't think I'd buy a new one - let someone else take that initial depreciation.