There's two approaches to this, especially in a light car. The first is the traditional way, which all the posts so far have been about. The second is the way some pretty successful flatties here in New Zealand have gone about it. Keeping the stock 3 3/4" Ford crank, standard overbore, and concentrating on revving higher and producing hp from those high revs. Torque is not so important in a light roadster, so hp at higher revs becomes the goal. I know of several flatties here in NZ that approach it this way. It's not necessarily any cheaper, blueprinting and all the mods needed for this are spendy, it's just a different approach.
In my opinion, unless you particularly want to be period correct, replacing the early trans with a T5 or (in my case) an F150 3+1, is one of the best mods you can make. I can slam through the gears knowing it aint gonna break, and the overdrive makes highway cruising a real pleasure.