408 stroker vs. 500 stroker Challenge fun!!

First let me say that I admire your goal of making this a fire breathing street mostly/strip car but I think that your 5K limit might be a little conservative even just for the tranny and engine. To build the tranny to take the extra torque of a stroked SB or BB I would budget for 1-2K. This would include the Red bands, steel drum, bolt in sprag, shift kit, extra capacity oil pan and a good name brand high stall converter (6-800$'s). Then figure in a set of either TTI or fenderwell headers (the bigger the better remember it's a stroker) and you're approaching 3K. Now we're into the engine stroker kit, aluminum heads (tons of choices there), camshaft (solid roller), roller rockers, intake, carb, high volume oil pump, high volume water pump, aluminum rad cuss she's going to make lots of heat, see where I'm headed. Personally I'd be looking closer to 8K.
If you want to leave "bad assed" and "fire breathing" out of the build then you might be able to go the budget build route but she'll be awful tight. IMHO
x2