1
) I don't know, but make sure you choose a place that will give you a good fit on the bike as well. I would expect a fit to be included for free with the purchase of a bike as well. If they say otherwise, run away. I haven't been there, but I feel like Cronometro would be a good place. I haven't been impressed by any other shops in Madison
(Machinery Row <--expensive, Willy's <--crappy mechanics, Budget <--do they have tri bikes?
). While there will be some great deals online, I would avoid them this time simply because being able to get a bike fit from a local shop will be very valuable.
2
) Definitely a tri bike. There's no reason to incrementally work up to the right bike unless your budget demands it
(yours doesn't
). With a tri bike you will have superior aerodynamics and the steeper seat tube angle will make it easier to run after the bike leg. You can jury rig a road bike to approximate tri bike geometry, but why do that when you can just use a tri bike in the first place?
3
) The best time is between now and a few months from now. Next year's models are coming out so bike shops will offer discounts on this year's models to make room
(I know Cronometro is having a Cervelo sale, btw
). Also the tri season is ending, so the demand for gear is dropping off, so the prices should come down as well.
4
) $2000 is the regime where you get the best bang for your buck, so you should find a bike that will last you forever. Paying much less
(<$1500
) will give you a significant drop in what you get, but paying more
(>$2000
) will start to get into the diminishing returns zone. You'll get better stuff, but it will be only a little better. For $2000 you should be able to get an aero frame, vision tech bars, good wheels and at least an ultegra drivetrain.
Edited by skavoovie 2009-09-18 3:40 PM