I know what your saying. You keeping loving them more over time and want to know everything.
I can't find the thread. I would just read up on some posts here since a lot of people have mildly upgraded 350 tpi engine and discussed results. Chevy made 87-89 Irocs/z28 with 350 and t-tops but 90-92 z28s were hardtops only. No manual transmission with 350. I forget if you could get a 90 z28 with t-tops and 350. 87-90 have different ground effects/spoiler than 91-92 so you can narrow down your search based on preferred look.
-I would not invest any $$ in upgraded stock heads. They are good for mild power boosts. If you decide on more power (300+ hp) Vortec heads are good for price but you need different intake base so at that point other budget aluminum heads might make sense.
-cam swap will increase power a lot. I think LT1 Hotcam or ZZ1 cam are the most aggressive cams you can use without reprogramming computer prom.
-shorty style headers will flow good and fit well.
-TPI intake is restrictive on a 350 and power falls off at 4,500 rpm. I would get aftermarket runners that add power and push it up to around 5,000 rpm. TPI runners were only designed for a 305!
-stock TPI intake plenum and base flow good but you can port them to make transitions smoother and help flow some more.
-you can cut off lower air baffles underneath air filters to help flow.
-although you can run dual exhaust pipes, under body is made for a single pipe after catalytic converters. There are a few aftermarket catback kits with 3" or 3.5" pipes that would be fine.
-transmission and rear end are good to around 300-350 hp. I would get an aftermarket rear end cover to help strengthen it.
-$120 cam
-$500 headers
-$400 bigger runners
-$100 adjustable fuel pressure regulator
-$600 catback with muffler
-$130 aluminum rear end cover
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$1,850
This should get you close to 300 flywheel HP where stock is 240. I would not spend a whole lot of money in case you decided to seriously upgrade at a later date. That way you haven't spent too much now for some fun

Keep us updated and let us know what you buy!
Also, to me people are asking too much for thirdgens. Unless really taken care of they seem to all need new headliner, torn seats, bad tires, worn brakes, need body paint and some rust. I would use these to argue price down.