I'll go along with that "loaded question" statement.
Before making any specific recommendations, I'll ask ya a couple of questions.
What year truck?
Will it be a daily driver or a weekend cruiser?
Is mileage the most important criteria?
With those questions remaining unknowns, I'll give you my opinion (and that's all it is, just an opinion...and everybody's got one.) First, I'd go with a 350 motor. Any increase in mileage you'd get over a 283 or especially a 305 would be marginal at best. And the additional torque of the 350 would (again, in my opinion) make it worthwhile.
Second, if you want the best optimization of torque ("pull well") and mileage, a stock setup is probably the best compromise. Either that or a mild "RV" cam that has something like 210 degrees of duration on both exhaust and intake and a lift of around .450. Lobe separation is kinda academic on a mild cam like this. 110 degrees or thereabouts is the normal LSA and has worked well on the cams that I've used.
Third, the carburetion issue will have a lot to do with the end result. Some folks are fine with a 2-barrel carb for economy...I prefer a 4-barrel with small primaries and larger secondaries so that I have power on tap when I need it, but can get acceptable mileage if I keep my foot out of it. I prefer AFB (Carter or Edelbrock) carbs, but others prefer Quadrajets for this type of application.
Predicting mileage without knowing some of the variables is almost impossible, but I'll just mention that for my truck (64 C10, 282 I6, Carter 4-barrel, headers, 4-speed and 4.10 gears) 15 mpg is about what I get in a combination of city and highway driving. It doesn't seem to vary much one way or another from that figure.
If I had my way, I'd prefer to have a lower numerical rear gear...something like 3.08...but not for the sake of mileage, but rather the ability to cruise on the highway without spinning that long-stroke motor at high speeds for long periods of time.
If you're asking about which transmission to use, the TH200-4R or TH700R4 are good choices because of the overdrive top gear. Tha would allow you to run a steeper gear (3.73 or 4.10) and still have a decent top end.
The summation of all of this is that the components all have to work as a package to get optimal performance, whether that means mileage or power. And if you want both, you'll probably have to make some concessions in both areas. It's hard to get real good mileage and have a real powerful motor/transmission and rear end package all at the same time.
I dunno if this has answered your questions, but it's given me a few minutes to avoid doing any real work.
