Thanks for the quick replies.

Looks like i'm definitely going with a road hub, sks fenders and some 28s. Tire recommendations?

The frame has a braze on for a fender on the top of the drop outs...I'm thinking with a long enough bolt i can use it for rack + fender? and i have a C shaped adapter that clamps on to the seat tube and provides a securing point for the top pair of bolts for my bolt-on rack. I HATE clamp on racks. Heavy useless high center of gravity POS. If i can't get around the bolt on rack issue my whole project is borked and i'll have to sell her ;(

Cool beans!
http://www.velo-orange.com/ter5brnumo.html
http://www.velo-orange.com/ter5exlorebr1.html

I'm probably just going to rock a 7 speed drive train. If anything breaks i'll bump up to an 8 w/ some bar ends.