Well Nate, it sounds like you have quite a few good pieces of a big puzzle figured out. Listen to the few people here with the most experience with 302/347 Explorers. You are right that Brad will have the quickest NA 95-01 Explorer soon, and I helped to steer him in that direction.
Most of what's in this thread is comparing apples to oranges. The 2002+ trucks are vastly different. For a NA 4500lbs truck, those have a notable advantage in their trans. The V8 five speeds have similar top four gears to our 4R70W four speeds. Their 2nd gear is about the same as our 1st gear, that's a huge starting line advantage. It helps for towing as well. Leave out boosted trucks, that hurts the five speeds, literally.
Concentrate on what Jay tells you, evidently you have discovered the greatest wealth of knowledge you can for big engine power. Jay Allen is far better at selecting heads, cams, intakes(not air cleaners), headers, exhaust, more than anyone here or there.
The GT40 heads suck, as do the GT40 intake(not air cleaner), and cam and headers. That is my opinion, and I guarantee you that Jay will agree with that. The GT40 heads and intake will produce GT40 302 power on any 302, that means 240-300rwhp basically for normal builds/rpm, with Jay's cam.
If you want better power, you need to greatly increase the airflow of several parts, not just a couple. The TFS heads are about the best choices you can make, the Twisted Wedge heads are the best for an Explorer given the port locations. High Ports would be better, if the ports weren't .800" taller. Toss the intake, find a high rpm short runner intake, and match it with Jay Allen's cam made specifically for that intake, the heads built by him with his valve springs, and bigger headers.
With that kind of combination, then you could see 14's easily with a 302. But I don't think anyone is going to spend that kind of money on a stock 302 shortblock Explorer, or build headers. The exhaust from the cats back can be just fine in an Explorer, there is room. The headers and cat pipes though are serious restrictions to airflow.
A 302 engine isn't choked off so much with the existing headers available, compared to any other V8 or boosted engine. Those headers are not capable of efficiently producing the kind of power the higher flowing engines are. A 400hp 302 from your average strong street Mustang will not produce 350hp in the Explorer with the common headers. That is a massive restriction caused by the lack of space in the engine bay, and the choice of the header makers. They want to make a 1.5" header only and convince you that it's good enough. Fine, it's good enough for them and you. I wouldn't install a 1.5" header on my stock Lincoln LSC(302 HO). That's a shame we have to put up with that, but that's business and the market.
Good luck Nate, I hope you get it done as you want it, and I hope it flies. Regards,