Have to agree with Dodj's 100k comment, the higher strung, higher revving, higher HP you make any motor you're losing some longevity in the process. How many miles do you plan on driving a 440 or stroker car per year? Gas alone would keep me from commuting with one, relegating it to more of a weekend car so I'm not as concerned about it lasting for high mileage. One thing about a modest stroker (500 ci or less maybe) is that you won't have to have as radical a cam or as high compression to make your numbers, the downside is that strokers do put additional loads internally so you'd want to go with higher quality forged crank, pistons, I or H beam rods, etc. to hold up. Me, if I build the 383 in my Roadrunner I'm going with a modest 438 CI to keep things reasonable, that or pick up a 400 or 440 for even more cubes with a mild stroker.
Later, Jim