I appreciate everyone's help, and I will continue to read and learn more (don't we all?), but I think I do at least understand the basics, dished pistons are just rarely talked about. I, of course, will be talking to my engine builder. Its not like I will throw a list of parts at him and call it done. From what I hear my current build (I haven't updated it yet) is within everyone's suggestions, so here we go:
500" stroker kit, -24 dished pistons (should be slightly above 10:1 CR), around .040 quench
Bare Trickflow 240, with their valves, springs will be whatever is recommended for the cam
Cam around 240@.050, around .550 lift
Most likely Harland Sharp rocker arms, 1.5 ratio
Holley SD intake
Either 870 CFM Street Avenger, or similar CFM double pumper
440 Source stroker windage tray, oil pan, and oil pickup
1 3/4" Hedman Headers (I would go 1 7/8" but that would cause clearance issues with the pitman arm)
Edelbrock RPM fuel pump? (max pressure is 6 lbs, though)