Crank is shot, do I stroke it or not?

For me, the shortblock is what I'd concentrate on for now. I'd go with a stroker, torque is a wonderful thing. For that cam, I think the headers/rear/carb/etc you have would be fine. Yeah, the one-legger rear might spin more. The 8.25 might not last as long as the 8.75. Blah blah lol.
Do the stroker shortblock, spend what you need to on that, and enjoy it. Use whatever heads you can afford. Alot of people forget the heads/cam/rear etc can be upgraded anytime down the road, without alot of downtime. You don't have to place every upgrade you "might" need into your immediate budget.
If it were me, I'd build the stroker with what you have.