Small Block or Big Block- help me decide

If I had to pick between just the two, I'd go 360. Smaller, lighter, less of a hassle to fit components, and probably cheaper.

However, going away from that, I agree with j par's call for a 360 stroker. The 408 gives you a small block package, with the power levels you're looking for. That would get my vote.

If you had to go BB, RRR's suggestion for a 451 stroker would give you even more horses.