Maybe an MSF Course will help? A Smaller bike is easier to learn on than larger bikes, that's for sure.. The larger the bike the longer the learning curve. More due to the weight of the things and balance than anything..
But. If he's even average height, and more responsible, a 750 cruiser is a really nice machine to learn on..
The thing is with 250 cruisers is that they are cramped and have no real power. And lack of power to get a person out of the way of situations on the road can be a bad thing.. Nothing worse than cranking on a throttle to avoid a thing and nothing really happens..
Sport-bikes are different. A 350 would be power enough for most, but cruisers - I don't think a 750 and a bunch of parking lot practice to get a feel for emergency braking, tight radius turning, and balance - before hitting downtown traffic at rush hour, is too much of a stretch for almost anyone..
If he is taller and heavier even a larger cruiser is not going to be too much for him to handle..
A 250 though? I personally wouldn't..
People tend to outgrow those machines very quickly. If you do start there, most would suggest that you buy used, learn on it, and resell it for little-to-no loss a few months later when you want to trade up.
Last edited by Mark-B; 10-26-2015 at 08:22 AM.