In the performance game, there are lots of varibles. In addition to horsepower, torque is another factor. If fact, torque is the real key to acceleration. In other words, an engine that has less horespower, but more touque may make the car accelerate faster.
Gear ratio rears its head. If you have a high gear (low numerically) raito, an engine with a buttload of touque will really crank that gear. If you have a low gear (high numerically) more torque, though it certainly makes a difference, won't nessessarly make the same dramatic increase. IN other words, you may be pouring a bunch of gas through the engine, and the gain is almost nothing.
The torque/hoesepower issue is a complicated issue and lends lots of varibles. If it were dropped in my lap, this is what I'd do:
(You can install newer blocks in old cars without modification. I don't recall what you have to do, but you cannot old into new without some modification, either new mounts, or something.)
I don't know what kind of modifications you have to make to go from powerglide to a t/b 350. I think that the shifer works, only that the markers/indicator don't align, so you have to feel it. Again, I'm not postive.
Another thing I'm not sure of is crossmember/driveshaft configurations. I do know, however, that you can it's a bolt-up application to the powerglide. Also, f/g cars are some of the easiest cars to install engine transmission combinations.
Two senerios that I would take: If it weren't lots of money or changes, I'd drop in the 400/350 and see what happens.
If I were flat broke, I'de hook up the powerglide to the 400 and chunk it in. I don't know that much about powerglides and how druable they are, but to get back on the torque issue. The powerglide can be viewed as the high gear raito senerio: such a combination might make for a quite potent set up.
It's not like some of the more miserable engine installations of other cars. Because it isn't orgional, I view engines/transmaissions as disposable parts. Just like brakes, if you wear it out, put a new one in.
The point is that if you already have the parts, and you have the skill level of a good shade-tree mechanic, dropping in an engine--just to see how it does--it isn't that big of a deal if you're not satisfied with the results. Simply change it back.