1 a. I had to get the transmission rebuilt shortly after I bought it. After all was said and done, it ended up being $3k but I'm not sad I did it. I did get a few things done at the same time though. I'd recommend getting the rear main oil seal replaced (requires the transmission be pulled normally) and flushing the fluid lines. If you're interested, there ace shift kits available that will make for crisper shifting that may not cost you anything in labor. A transmission cooler may also not be a bad idea. If the guy does other gear-type work, have him check out the drivetrain and see if anything else needs TLC (rear axle?).
1 b. I talked about the possibility of buying a used transmission with the guy who did the work too, and ended up deciding against it primarily because you'll be inheriting the last guy's problems. Most places that sell used transmissions will offer guarantees and give you a new one for free, but you end up having to foot the bill to have the bad one pulled and the replacement reinstalled and probably even shipping back and forth. In addition, the mechanic will likely not cover any problems you have later. On the other hand, if you have it rebuilt, your shop will likely offer an extensive warranty and at minimum fix any problems that arise in the near future. So a used one could have half the cost vs. a rebuild, but if anything goes wrong that savings disappears. The shop I went to even gave me a 100k mile warranty that could be redeemed nationwide
2. I think that I've seen that it is possible, but I can't see that being cheap

If it's something you're interested in, though, it's worth asking the shop about.
3. An engine swap does seem like overkill if it's running fine since you probably wouldn't be saving a lot. No idea if other engines will fit.
Cheers and let us know how it goes!