Thanks for resurrecting this thread as I'm in the same boat. After much searching, I've narrowed it down to between Kona's Jake the Snake and the Trek Portland... I agree that the Specialized Tricross Sport is a little pricey for the Tiagra group, but I still haven't fully crossed it off... the Snake's about the same with 105 -- and the guys at a LBS in Boulder found that that the front shifter can handle a triple, which I plan to swap in (with new derailleur) if/when I buy it... it'll add some bucks, but I'm pulling a kid and trailer and need the granny gear for some of hills/mountains around here. The Portland's already got a triple, plus disc brakes, but is way pricey. But I have to admit there's something about it that speaks to me. I also plan on pulling a trailer when touring (which may be awhile til the little one gets older). The only thing is the wheelset, which seems a little light... decisions, decisions...

And anyway, I've got an older steel lugged beast (early 90s Miyata Triplecross) that I can use for the expedition-style tours... I just want something lighter to pull the little one with... well, that's a rationale for really wanting a new bike after sixteen years!