So I just picked up a 68,000 mile, 1987 Trans Am, 350 TPI with a 700r4 Auto. I love the car and I have been recommended a Vortec head swap. I'm not looking at increasing the power a ton, however, I do want maybe 50 more horsepower, what would you recommend I do to do this, relatively inexpensively? Thanks!

Full bolt ons and get rid of tpi for a shorter runner intake would be a good start and gain a good amount of power pretty simply. Mild cam and tune on top possibly get you 50 hp gain total with the bolt ons.

Swap to the vortec heads as recommended. Since the bolt pattern will not line up with the factory lower intake manifold, search around and pick up an Edelbrock 3806 (I think) lower intake. These can be found for around $500 used as edelbrock no longer casts these. Arizona Speed and Marine sells enlarged runners for about $375 new. Invest in a die grinder of find a machine shop that can port and polish the lower intake to match the larger runners. Port the upper plenum while you are at it. Free up the exhaust by removing the restrictive exhaust manifolds and replace with some headers. I used Dyno Dons, they fit good and look great. Don't forget to free up the rest of the exhaust system. Give the car a good tune up. HP ain't cheap. These mods will get you to your goal or possibly beyond for around 1500-2000 dineros. Do searches on this forum for details about the specific parts listed. Good luck!

x2 look for good used TPI parts. Some guys are off their rocker with asking prices, be patient.
Sellers can yell rare all day but how many are lining up to buy them?

Small cam, exhaust and as said some home porting and patience will get you a decent running tpi. Torque is cheap to build, hp (rpm) isnt