Here'* the deal, no matter how much TLC I give the machine, it looks like it may not go through another winter :

-Transmission has a hard time shifting in first gear when cold, sometimes won't and I have to fiddle a bit. It also definetly won't go in reverse when cold.

-Piston rings are mostly shot, takes some cranking to start and smells like unburnt gas for a while until warmed up a bit. I guess piston rings VS ignition because power'* there when I need it and it doesnt misfire.

-Supercharger is eating itself up slowly.

-And then there are wheel bearings to do, rear brakes, rack and pinion...

From your experience, is there a point where someone should start looking for another car or its just a patience thing and with some parts from time to time it can (in all consideration of reliability vs age) defy time?

I love this machine and the more parts I put in it the least I wanna let it go but damnit, is it worth it? It still stays cheaper than 400$/month + insurance but it eats lots of time.

Until now I changed :

-Water pump, radiator and heater core
-All 4 struts for KYBs, coils for Moogs, top plates
-Front discs, pads and all brake lines
-MAP sensor
-Fuel pump and fuel lines where they go in engine bay
-Alternator and battery

And probably other stuff I don't remember!

I don't see how you could smell unburnt fuel due to bad piston rings. Do a compression check on each cylinder using a cylinder compression gauge available at most parts stores. Smell of unburnt fuel is an indication that the ignition system is not burning all of the fuel or the fuel system is dumping way to much fuel.

What is the supercharger doing??

I'm not sure about the trans. When was the last time it has been serviced? Fluid/filter change?

Wait, are you sure its an L67 Series 2? I thought the 95'* only came with the Series 1 */C engine.