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Instead of a triple have you considered a compact double? It should shift a little better and will probably mean less shifting overall, might not be suitable if your doing a touring ride though.
I have a 2007 specialized allez elite that i bought used a year ago and have been super happy with. With your price range it shouldn't be hard to find something that will be comfortable to ride all day for a few days in a row. At a minimum i would look for a carbon front fork, carbon seat post and seat stays, for the added comfort. I would also buy the bike a few months in advance so you can get used to it and make any necessary adjustments.
Also, find a good bike shop that will allow you to test ride outside the parking lot, preferably for 20 or 30 miles so you can get a real feel for the bike and to make sure your comfortable on it.
Good luck, sounds like it should be a fun experience.
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