BB71 - I agree with Moper's reply. There are many unforseen costs involved in building a good strong short block. Without that solid platform, for your motor, you will end up with an unreliable unit as some others have told us about. I spent approximately $6500Canadian on my short block 451 stroker. And yes I got a very strong unit here now. Bought the best parts but the crank is an original 68HP 440 crank and the cost for that was small. Things like a good oil pump, new pickup, windage tray, good timing gears, good lifters, oil pump drive, etc, etc - all need to be replaced if you want the most reliability. The machining and balancing costs are expensive if they are done by a reputable shop. Then you have the top end to look for - as someone has already mentioned. To feed a good 500" motor you are looking at a carburetor in the 870 to Dominator sizes. They are expensive. Headers from TTI are at least $500US uncoated. Then the tranny needs to be upgraded to handle the power - and the diff. Anyway you should have the picture by now regarding budget.
My advice - freshen up the 440 put it in and have fun. In the meantime build up the 400 block slowly as time and money permit. Trust me, even a stock 375HP 440 will bury you into the seat with the fun pedal pushed down. Whatever you do, the best of luck. Good to just see another Mopar back on the street.