If you want to stay with cruisers, try looking at the Kawi Vulcan 500cc, or the Honda Shadows (600-750cc). You will get used to the heavier weight with time, but if you have to work as hard as it sounds to get the bike off the stand, I would say it isn't fun. I had that happen to me when trying to sit on a Yamaha SomethingHuge cruiser at a demo. I figure if I can't rock it off it's stand, I don't want it--even if I can ride it.
On the other hand, take a look at other cruisers in the 950's class, and try sitting and righting those. It may very well be that you need to practice a different technique than you used with the 250. The 250 is probably light enough that you can muscle it around with mostly arm strength, like a guy would. Your strength is in your lower body, not upper. All cruisers carry their weight low, so if you use your legs and hips to help you rock the bike up, you may be surprised at what you can do. That Yamaha is the only bike I've ever had that problem with, and it was a shocker. I'm pretty strong, grew up on a farm, around machinery, etc. I'm also kind of short, with short arms, so it may be that I just couldn't leverage my body the way I wanted.
