I'm in the middle of a similar rebuild myself, except I won't be having the block bored. Mine is in pretty decent shape, no ridge ring and fairly good on out-of-round/out-of-taper spec, standard bore. I think a quick run-through with a hone will give it some cross-hatch. My parts list so far:
Comp 268H square pattern cam, lifters and timing set, $217
https://www.summitracing.com/parts/cca-sk12-210-2
KB Claimer +7cc flattops with rings & wrist pins, $249
https://www.summitracing.com/parts/uem-9901hcktmstd
0.028" compressed thickness head gaskets, around $70/pair
https://www.summitracing.com/parts/nal-14096405
With a pair of craigslist Vortec heads I picked up a few years ago for $250 and had the local machine shop do a 3 angle valve grind, decked and hot tanked with new springs and keepers for $300, I'm expecting in the neighborhood of 10:1 compression ratio or just under. The cam I picked will work with Vortec heads lift limitations. And even though Rusty Nail may sound like a nut, I'll be opening up the top ring gap to 0.030" and the 2nd ring gap to 0.035" just incase I want to add some giggle gas down the road. I already picked up some items but plan on replacing the water pump, oil pump and fuel pump, as well as a reman crank. Upon inspection/measuring if the crank is OK it may just get crank and rod bearings and save around $100. As for the trans, I rebuilt it a couple years ago, performing several mods that should help it sustain into the 500hp range, setting it up for dual-feed, increased the line pressure a little and dropped out the check balls for harder hitting shifts (something you may not want, it hits HARD). For a converter I've been eyeballing Summit's 2000-2400 stall at $230:
https://www.summitracing.com/parts/sum-g2700-1
Should work good with the cam's powerband. I'm hoping this setup will keep me in Street Class at the mud races but may end up in Hot Street if it won't hold at least 17" of vacuum. With no class limitations other than "6 cylinder" and "V-8" for the additional Hill-And-Hole competition, a 100hp or so shot of nitrous should make for interesting launches off the jumps. If you didn't want to bother with trying to find a good set of Vortec heads (since they're susceptible to cracks) Summit sells a nice set of Vortecs that have great reviews, and able to handle up to 0.520" lift:
https://www.summitracing.com/parts/sum-151124
Hopefully all this will give you some things to think about and compare. I'm hoping to have it reeled in for around $1500.