One thing nice about old trucks like this is the louvered hoods; heat doesn't build up like newer rides. The TH400 is great, as is the GV overdrive, but my preference would be a single piece unit like the 700R4. And yes, part of the reason is that I'm cheap. The 700R4 doesn't withstand tremendous torque well, but I'm not convinced that I need to develop all of that torque potential. (I just went through similar questions with the Cad 500; this is another long stroke engine.)
I do have the Leo Santucci book on hand, and yes, it is full of valuable information. TRW's website indicates that they no longer make engine componenets, so I assume that the 2199f pistons are vintage, but are probably findable in some warehouse. I looked up the Innovative Turbo exhaust manifold, and I'll probably go with that. I also like the notion of using multiport EFI.
By nature, I like the sound of a smallish, oversquare engine that happily buzzes up into the stratosphere. With the 4.56 axle and probably 31 inch tall tires, I've got plenty of leverage, and so may not need torque. Destroking the tall deck and building a long-rod rev engine would be my inclination. According to Santucci, this was the original method for getting more power from the 292 block until better rods became available, when all switched back to long-stroke designs for drag-racing torque.
The operative question then becomes go with my inclinations, or go with common sense? I would assume that a high-winder would work well with a 700R4 as it can downshift to give the leverage needed for high outputs, but still have overdrive for the bulk of the driving time at moderate output levels.
I'm not too worried about towing with excess boost; I wouldn't be pulling enough trailer to need high horsepower for long periods. Just the occasional blast to pass a foot-dragger or to get up a hill. More of an everyday automotive application than a semitruck application calling for massive horsepower for long periods.
