Smoke out the pipes? Worn valve guides most likely, not leaky gaskets.
Requires machine shop to install. You can add "umbrella seals" to the valve stems (Chevy uses useless O-rings that do nothing) that will keep most of the oil from splashing on the stems and running down in the guides. The seals are only a couple of bucks at the local parts store, and take an afternoon to install if you're mechanically handy. It's not a bad thing, there's 15 zillion engines out there with bad guides just like it.
Tranny, on the other hand, I'd be more leery of. If it's the original 700R4, they are not electronically shifted. The only thing electronic is the torque converter lockup, but that's not the problem.
Most likely the throttle valve (called "TV") cable is either misadjusted, or the trans is suffering the effects from misadjustment. The cable goes from the carb to the trans and regulates the trans fluid pressure in the valve body, basically telling the trans when to shift. If it is not adjusted properly, major trans damage can occur.
It is very easy to check and adjust. Do a google search on "adjusting tv cable".
Neither problem sounds like a deal breaker to me, even though the early 700R4's were a POS. I have had several "beater" Chevies like that one, and have a '93 WT with a 4.3 V6/auto overdrive now. Love the truck; easy to work on, plentiful parts available cheap and smokes enough to block out the sun when it starts up (same problem). And I'm a Ford guy.