If you buy used and you know what you're looking for (and therefore, what fits you and what doesn't), you can get more bike for your money. The downside is the lack of a warranty, since that only covers the original owner. The other issue is that the sizes often aren't there. It's hard to find anything smaller than a 58cm around here.Other concerns is crash history (more important with carbon) and storage. Make sure to talk to the seller to make sure that it's actually their bike that they're selling.
New, you have the benefits of a warranty and going through a bike shop for free adjustments, etc, as well as the fitting process. Helpful if you're not sure what might or might not fit. The downside is the money.
Trek vs. Specialized: Both are good brands, and within a given price range, they're going to be comparable. What makes one better than the other is how well they fit YOU.



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Other concerns is crash history (more important with carbon) and storage. Make sure to talk to the seller to make sure that it's actually their bike that they're selling.