The guy that holds the lap record for 600 ss, 600 sbk, and 750 ss (on a 600) at PIR started on an SV 650. Not bad for someone that never logged the required time on a scooter, 125, and 250.
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At moto GP level it's usually different and nearly all the top riders start small, but in any case you're wearing your track head again. Street is different. If you ever took your helmet off that little fact might one day get pounded through your skull. Track is a lot less scary and doesn't inhibit you as much as the street. And the part of the learning curve that has you sliding along the track before you get up and get back on your bike often has you sliding into something hard and bone breaking on the street.
I can say you will probably never be fast on the street because on too fast a bike you won't learn how to read and anticipate traffic flow so that you're always in the right place at the right time and in the right gear. Search long enough and you'll find an exception. Jesus was an exception to the fact that we all die eventually and resurrection isn't an option. Most of us aren't Jesus.
And maybe if you'd started on a small bike you wouldn't be trying to convince a bunch of enthusiastic amateurs on an internet forum but be a pro racer instead.
AV8r - a 250 can go down in a stall or something similar. It's a lot less likely to than a bigger bike, but if you're a touch slow getting a foot down you'll go over. New riders especially are often a touch slow. No real harm done usually, but it's easy to lose a strip of skin from wrists or ankles so don't use the fact that you're on a 250 as an excuse not to wear boots and gloves.
ShinobeJeh - yeah, I bent a little. I don't have a problem with the size and weight of any bike for a newby. A day on a borrowed small bike to get the basics and build up some confidence, then a couple of days of decent instruction can get you doing full lock figure eights and the like on any bike. It's real easy on some of the big Harleys. The issue is the power on the street, so my very hesitant view that in some circumstances the 650 can be sort of OK is for the guy who's going to ride cruiser style with no interest in ever being a little bit quick. Trouble is, that sort of rider shouldn't really be on the 650 anyway as it's wasting the bike's potential, and one day he might decide to use some of that potential without really having acquired the skills to..
Swagen - At 60 on the highway the 250 is cruising very gently and very quietly. It'll cruise at around 80 comfortably enough with a good reserve of power for getting out of trouble if you're daft enough to get into trouble. You won't outgrow a 250. You will go through a period of being bored with it because you build confidence much faster than you build skill, but you pass through that and start to realise just how good and how much fun the 250 really is as your skills catch up. That's the point when you're ready for a faster bike - the time when you're wondering if you really need one rather than knowing that you want one.