Lots of ideas flowing now. I'll give some perspective from my point of view. The whole low RPM torque deal isn't as bad as I thought it might be with the LS. Provided the gearing is right. Off road, I've not found myself wanting for more torque. I may dive into low range sooner than Larry does with his 8.1, but the 4.10 gearing and low range of the 241 really does help. Kinda wish I went 4.56's with the OD of the 700r4 would have kept it in check on the freeway. Still off road, I've not had a problem running the 5.3. On the highway, I can keep up with traffic just fine, but if the grade gets steep I'm whipping that 5.3 like a rented mule. It's out of OD, into 3rd or 2nd depending on the terrain. I know the engine can handle the RPM, but it's another area where more gearing would help. I will say this, it's way easier to keep up with the 5.3 than it did with my q-jet 350 in the old K5.
An 8.1 really is ideal in the stock form you got 400 lb/ft right off idle up to 4,000 rpm. Even with a 465 trans you can keep it rolling without much effort. No modifiying required, other than getting a good tune the engine is good to go right from GM. It's not an LS, but uses the same exact technology as far as the engine management system goes. Same ECM, same firing order, the same type of sensors. The only thing it shares with the big block family is the physical dimensions. It's really the big block LS engine as it has more in common with the LS as far as how it runs than a 454/502 or any older big block. It's a bolt in solution, but not without it's costs. Aquisition cost is steep usually. The truck accessory drive system is not ideal for a squarebody. Larry's solution using workhorse accessory drive brackets is going to dry up soon. There's an expense as well as the chances of finding a low mileage 8.1 is going to be harder to do as the days go by.
One not so looked at option is the L29 Vortec 7.4 big block. Again, a bolt in affair with a squarebody friendly accessory drive setup. Vortec big block heads carry the same concept as the 350 Vortec heads do by keeping the port volume lower for good low-end torque. It's often overlooked, but solid choice for an FI big block swap. It's a tune away from even more power. The 465 will fit with the same clutch you already have too. Not as much demand for them either with everybody flocking to LS power too.
Sticking with the traditional SBC, ideally, I'd start with a Vortec block. Yes, some of the later TBI's could have had Roller cams, but all Vortec's had roller cams. You don't have to use the heads if you don't want to deal with the intake bolt pattern. Many aftermarket heads flow just as good as a Vortec or better for the same money as refurbishing a set of Vortecs plus the cost of the upgrades needed to run a cam higher in lift than 0.490 or better. Still, if you shop around you can get a Vortec specific intake for under $200 if you go for the power plus brand. Run a FItech or Holley system and it should run similar if not better than your existing TBI 350. This option would be the least expensive route as you can reuse a lot of stuff you already have. Accessory drive, starter, exhaust, ignition system, flywheel/clutch are all stuff you already have and are running now. The cost would be in the aftermarket injection system, but like you said you got the right tank to do it with.
Money no object, I'd be putting in an 8.1/nv4500 combo. But working the family budget the conventional small-block wins out in this race in my opinion. Mark knows them well, drag raced many and has a pretty good direction to start with. The big change would be the aftermarket injection. It would take out the limiting factor that a stock GM TBI system is. Even with the salad bowl mod, adjustable pressure regulator, and other mods, it's still a system that dates back to the 80's. It lacks room for growth and can't self-learn/adapt like the new technology can. It really gives new life to the existing platform by making a viable alternative to the LS swap.
So here's my idea for a small block. Roller Vortec block, small overbore to clean up the block, 9.5 Compression with aftermarket heads, roller cam ground for torque and an aftermarket self-learning 4bbl efi system. I think you could hit the target power/tq levels easy and keep the truck pulling well on the hills and still be docile enough to creep around in low or double low range and granny gear at no more than an idle speed.