Attn OldSub,
I'm a little bit confused by your statement above
"With the stock motor you aren't going to be able to haul much with anything much more highway friendly."
Do you mean that if he changes to a higher gear, he will no longer be able to haul much ?
When I was a teenager, I hauled plenty with my 54 Chevy Handyman Station Wagon, I don't remember what year end it had, but it cruised comfortably at speeds over 70 with it's stock 235 and 3sp. I pulled trailers etc. No problem.
Rich, I would say put in whatever gears you want, if you decide that you want lower gears afterward, you can always switch back.
Chris