383 to 496 stroker, streetable?

For me the issue is piston height. You have the biggest bore, and the shortest piston in one combination. It's so short there is no skirt really (less than 1 1/4" compression height), and the piston pin bore goes thru the oil ring groove. On a racing engine, that's no issue as the mileage is low and disassembly is fairly regularly done so piston and wall wear can be kept track of. On a street engine, you really can't run a tight quench because if you do, the pistons wear a small amount and then they rock in the bores (all engines do this at TDC when the piston changes direction) and it's very easy to hit the heads with the pistons. Less quench means more tendency to detonate too. If it were up to me, I wouldnt go past 3.915 stroke and put a set of heads that will feed it well. It's less of a hit on the tires, can run the factory oiling system (including the indented pan for the idler arm), will perform very strongly with a set of mildly ported RPMs or SREZs and will last forever.