Thanks a ton for your reply and sharing your experience!
I like the "buy once. cry once" line, and I think it basically sums up my mentality on this rebuild. With that said, I do think I'll probably be buying pistons, and have been looking at rotating assemblies that include the crank, rods, pistons, etc. Now I just have to try and figure out once and for all if I can actually stroke this legally in CA. I've done some engine shop hunting and found a couple places that look worthy of my cash, so I'm going to give them a ring and ask them if stroking it out to 408 is possible with CA emissions. I think I was trying to figure out too much all at once when I initially posted this thread, its not like I will be doing the actual building of it (unfortunately, I'd love to but don't have the space nor equipment to tackle that learning experience), so I will consult with some builders and see what my best option is.
As for a MAF swap, I haven't researched enough to know for sure, but CA smog seems to make things way more difficult than they should be. I'm not 100% sure but it looks like I'd have to track down a different EEC than the fiveology kit has, the EEC I best suited for me here in CA seems to the BIO0 (comes from a 1995 CA 5.8l MAF truck), and the cheapest one available at the moment is 400, others are around 700, so putting together a kit with that EEC would be close to 1000 dollars unless I start hunting the junkyards and get really really lucky. I'll probably just stay SD for now, but I have sent an email to fiveology to discuss the smog legalities of their kit for a CA build. We shall see..
Looks like I need to start reading up on torque converters :)