Helping a Man Pick a Bike

[tulip]

He answered his own question: touring or cross bike.

I'd tell him what I tell everyone: go ride lots of bikes (with an open mind) and see what feels right. Ask questions, and listen to what the bike shop people have to say (sounds like he has already formed many opinions). If he wants this bike to be The One for the next 30 years, he'd be better off working with a good LBS than buying something off ebay.

Trek touring bikes, Surlys, and Jamis are all good places to start.

[Bike Chick]

I would add Gary Fisher Crossbike and Salsa to that list.

[alimey]

The other thing I would add is that the critical measurement is the reach (ie; the effective top tube). Now that some frames slope & others don't, the notional size of a frame (as measured via seat tube length) doesn't mean a lot, as bikes which sound like they are the same size can have very different reach. For comfort the new-ish compact drop bars might work very well for him. They have the nice round shape I am sure he like (vs the anatomic shape) & the shallow drop means the drops are more usable.

I would add in the Specialized Tri-cross - we have seen a few customers w/ these & they are very nice.

If his daughter is 5 she is probably on a tag-along, so depending on the type, he might need to steer clear of a carbon seatpin.