Matt - where have you found good 3.55 gears for $250? was there an option for the 60's trucks? what makes you think a junk yard find wouldn't already be worn out?
I said nothing about an automatic - you already have everything for a manual trans except the correct factory OD, an option for many years - likely have to change the drive shaft length, but otherwise a direct bolt in, no grief, and they've been offered in the swap here for $1-200 .... if you find an OD from 68 up it even has a syncro 1st
Bill