Jarrett, thanks for all of your input! My biking brother has read this thread and he liked your input a lot.
I appreciate everyone's thoughts here, also. LOTS of good stuff to think about and consider.
Where does a Sully Cross Check fit in the general scheme? My brother found one tonight - a 2015 model - that the owner is selling for $700 OBO... decent components and the right size. He's gonna go check it out on Thursday (he talked to the owner on the phone tonight) and said he might buy it for himself if I don't want it (we ride the same size).
Gary