Class awards are more possible, typically, due to the low number of such cars at any given car show. Winning a whole car show? There'll probably be a B-body with "wide valve covers" or 3 carburetors that'll capture everyones' fancy other than "a car like my grandparents had". Just the reality as I see it. Your experiences might be different.
In the later 1980s, I had had my '67 Newport long enough to get it spiffed up as good as I could. Had the orig vinyl roof scrubbed and coated in STP Son of a Gun protectant (satiny finish rather than the shine of Armorall), got the Turbine Bronze paint buffed and waxed nicely, plus all of the chrome. I'd spiffed the underhood, polishing the exposed metal a/c lines with red Scotchbrite to make them look nice, plus putting some satin black paint on the painted a/c lines. I had found a 1968 dual snorkel air cleaner, also nicely blacked and shined. I had put it in an indoor car show where we had a club display. So, it was pretty decent. Never got an award, but it was there "for the club".
When I'd take it to a local cruise spot, I'd park it in line with our other club members' cars. Hood up and all. I got lot of "My grandparents had a car like that" comments. I smiled and thanked them. Invariably, almost everybody would walk right past my car to head to the HEMI or 6-Pack cars in the line. So, at the time, I thought "I'm not going to the trouble to get the car out of the building to drive 2 miles and then 2 miles back. So, I just left it in the building, driving it when the mood happened. About the only place it "got any respect" was at our annual Mopar club shows, where people pretty much knew what they were looking at.
In this part of the world, Chryslers didn't get a lot of recognition in any show in the 1980s era. Even when our and other TX Mopar club people basically "grid locked" the judging lines at a big car show in Waco, one year.
In the end, though, the real joy or ownership is not specifically about how many pieces of "wood with plaques on them" which might be received at shows, but for the joy of the beauty of the cars, spiffed and shining in the sun, PLUS how great they drive on the road at speed.
Please your senses. IF others might notice and wave, wave back and smile. Driving these cars is the ultimate reward of ownership. Oh yeah, you'll have to "fix some things, too" . . . which can be ever more joy.
Take care,
CBODY67