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.