Hellfish,
I agree with you. I believe that a well set up 235 would develope the torque/horsepower to beat an equally built stock sized flathead.However, few people go to the considerable expense of building up a stock sized flathead. With this in mind, I would urge you to go to the trouble of finding a 261. About 50 years ago, Racer Brown showed us how to pull almost 200 horsepower (197 in fact)at a low 4500 rpm from a well set up 261 which had been bored out to 278 cubic inches.I've never seen a streetable flathead (normally aspirated, on pump gasoline) pull that kind of power.
With that in mind, I would like to make one suggestion. While the t-5 transmission is a fine piece, I think that the idea of the column shifted 3 speed has much to recommend for it. The flat torque curve of the type of engine we've been discussing make the additional forward gears almost redundant. If you stick with the 3 speed, however, go with the 1966 and later GM saginaw 3 speed. It too was available with overdrive (up to 1969), and the fully synchronized design is much stronger than the t-5! It was the standard manual transmission, even for the 427,big block full size cars, vans, 1/2 to 3/4 ton trucks, etc. Just substituting the 1966 and later transmission for the '65 and earlier (sliding gear design)can cut a full 1/2 second from your et! Just my 2 cents! (P.S.) If you want a Saginaw 4 speed with an overdrive unit already attached, I have one available! Call me @ (770) 683-7982