Investment-wise and cars are two terms that usually do not match up unless lightning strikes. Not saying it can't be done, but NOBODY ever considers the long-term care costs associated with owning a 1:1 scale model car. It's not as easy as it seems. If you're flush with cash and you see the car of your teenage years and want it badly, hey, it's only money. Spend it the way you want to.
Nobody knows what's going to be popular or high in demand in later years. But one of the biggest issues with these high dollar G-body sales is, some dorkhole with a clapped out 83 Monte SS with rusted out floorboards and eroded frame will see this sale and now demand 20K for his basket case just based on some of these one-off outlier purchases for some of these cars.
I've never owned an 83
H/O, but wouldn't mind it one bit. Came close a few times, but never did. Other than that, I can't think of another G-body I would go out of my way to want to get. Not saying I wouldn't like to have that 88 MCSS, but not at that price. I wouldn't pay it. I'd probably push a 25-28 spot max, and that is if it looked like it rolled into the showroom back in the day.