I'm a little late in posting my opinion, but here goes....I would class the VTR as almost THE perfect bike to learn and grow on. Its got a very neutral riding position, so it wont do your back in and you've got great visibility for commuting. It ain't the fastest 250 out there, but it's what you do with it that counts, and it handles like a champion through the twisties, even with my portly frame aboard.
Don't be put off that bikes wihtout tachos aren't true sport bikes. If you're riding hard (or properly), you want to be watching the road, not seeing how many RPMs you're doing, and you will learn where the best change points are based on feel and hearing.
Naked vs faired? There are times I wish I had a fairing (biking or full) as when you'rte riding in a good head or cross wind, it does get a little gusty, oh all right, it gets damn scary at times, but that's what motorcycling is about for me. When you're on a naked, ripping it up with the wind howling, engine screaming and kays evaproating beneath you, there ain't nothing like it
Commuting it's top of the board. Upright position lets you see everything around you. Masses of torque means you're not chopping through the gears every 2 seconds, just put er in 3rd and go. It's also narrow enough to fit (almost) any gap.

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