440 vs. stroker 408 build?

There's a big difference between "refreshing", "rebuilding", and "performance rebuilding". As long as you realize what you give up by spending less, it's no big deal. Wahtever works for you is what counts. The last "refresh" I did was about $900, but it didnt include replacement heads. Just oil pump, pickup, rings, bearings, gaskets, windage tray, cam, lifters, timing set, water pump, fuel pump, fuel pump pushrod, and carb. Make sure you either use a crank kit (crank and bearings) or have the crank turned and polished with new bearings. The kit's probably cheaper.