Thanks for bringing up the fit issue again, which is one reason why I've been thinking of *not* buying used. I like the idea of a real bike fitting you'd get at a LBS. It's still a bit too snowy and icy to test ride, but I sat on the OCR3 last week and liked it. I used a friend's old Giant for 2-3 weeks last year and I liked that as well.
I guess some parts of my question on whether the extra money for a nicer bike will depend on what they feel like when I ride. I'm just worried that with only 1 season of riding behind me I won't be able to tell. I'm worried that in year or two I'll wish I had saved for a Ruby or a even a Synapse 3.
With regard to the diamondback specifically, I wrote him to see if I can check it out next week. I figure if it goes before it wasn't meant to be...



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