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I've got a 4 year old 2200 that I just got a frame warranty on. So I'm hoping they send me a new frame like yours. I hope the carbon rear end makes it a little more comfy. Mine has been comfy enough anyway though.

It's probably not worth upgrading YET. Get your girlfriend some good brakes just cause you feel like it if you think she needs them. That sounds kind of cheesy to get yourself some nicer ones and hand the others down to her, especially since you won't notice a difference with Ultegra, they are exactly the same just lighter. The cheesy brakes her bike came with will wear out but they shouldn't be unsafe. If the two of you are strafing monster downhills braking technique rather than equipment is going to make the bike dangerous. You can stick Ultegra or Dura Ace pads in the 105 brakes if you want and have the same or very similar stopping power. The Dura Ace pads suck IMO anyway, I have run a couple sets of them in the past. I have Kool Stop "salmon" pads on mine now, they are great.

No need to worry about the wheels either until they break or you are really fast. I've seen people racing Cat 3 on unmodified 2200s before, so unless you're really fast it's not going to matter if you're just starting out. You'll want to have more experience anyway before getting a trick wheelset, then you'll know what exactly you want. As far as I know the Bontrager wheels should be fine. Mine came with Rolfs, with the old 2200s it would have been worth it to upgrade the wheels at the time of purchase if you could do so cheaply, as the Rolf hubs sucked. I've had to get the freewheel replaced and get the bearings and cones changed twice in 4 years. From what I've been told by mechanics though, the Bontragers are much better.

Spend the upgrade money on a road trip to go cycle somewhere really scenic.

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