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This sounds sort of like a problem someone over on Turbobricks had. In their case they nuked the trans by putting silly amounts of HP through it at a drag strip, but the symptom seem similar. When they tore their trans down, they found a clutchpack deep in the bowels of the trans with all the plates fused together. It had been slipping under power, overheated severely, and stuck so that it was basically in 'D' all the time.

I could see this happening if it was driven hard with low fluid. the pump was sucking air, couldn't keep the clutch clamped hard enough, so it slipped. Slipping under power (even if it isn't ~350+ turbocharged insane HP) for a while could have severely overheated it and fused it.

Probably not cost effective, at this point in time, to do anything other than get a junkyard trans and swap it.
--
'63 PV544 rat rod, '93 Classic #1141 245 +t

I would start with the transmission shift linkage bushings. There should be rubber "donuts" inside each of the flex points on the shift linkage. It's very likely that they are gone in an 88. I heat up these bushings first before installing them, it makes it that much easier. To adjust the linkage I put the car into park and move the lever on the transmission until it's in park, (don't quite know how you'll figure that out on your car; I don't think there's stops on to limit how far the lever can move, mine has never been this screwy.) Then change the length of the linkage to fit properly between the shifter and the transmission.

If, after you do this, it still does something weird, it may be a different transmission problem which I have no idea how to fix.

re: "...linkage seems normal and feels good and correct when i hold the lever underneath while it is being shifted. ..."

What do you mean by "correct", when you hold the leve underneath? It works normally?

A very common ailment is that the bushings in the linkage (outside the transmission) fail, and can give the symptoms you describe.

and re: "...and park if I "gun it"...."

??? Not sure what you meant by that, but another common problem is bad mounts (tranny and/or engine), which can let the tranny rock and upset the linkage, especially if you also have bad linkage bushings.