$1,400 for a 2005 with 5,700 miles on it seems like a good deal to me. That's what I paid for a '93 with 10K on it. Either I got a bum deal (though I don't think so given what other TWs are going for around here), the bike you're looking at is a "screaming good deal," or... and I hope this isn't the case... something is seriously wrong with it. I'd say at for $1,400, even if you had to put a couple hundred dollars work into it you'd still have a good deal. I think you could easily sell it later if you chose and not lose a dime.
If I may ask... what did you pay for the 2006 with just 700 miles?