Is there a reason it can only be 2-3 cars? I would personally spend some money building a big shop on my property with several lifts, and have a bunch of more modest cars that can all be a lot of fun.
2019 C7 ZR1, 7-speed
1996 C4 LT4 Grand Sport in blue, 6-speed.
1980 L48 4-speed Corvette in blue. Or another C3 that I can restomod with new drivetrain, suspension, brakes, and interior.
87-88 Pontiac Fiero GT. I used to see them brand new at the dealership every day on the bus riding to school, and I've always wanted one. I would totally restomod one to make it a 3800 supercharged Buick V6 with a 6-speed.
2003 SVT Cobra anniversary. I would take a convertible, but would prefer a hard top in silver.
93-95 RX7 Twin-turbo. These cars were amazing when they came out. 50/50 weight distribution, incredible balance, and pulled hard when the turbos spool, which was quick because of their inline design. The mighty ZR1 was faster, but every other Corvette would lose.
Datsun 240. Full restomod with a LS3/550 crate and ZF 6-speed.
I'd want some sleepers too.
My dad has a 56 Bel-Air wagon with an LT1 and 4L60e in it. I would buy that from him in a heartbeat if I had a place to put it. It is a beautiful and solidly reliable car.
I did build a Trailblazer SS several years ago and loved it and miss it to this day, but I would buy a Durango SRT.
Hellcat Charger. That's a sleeper, right? lol.
CTS-V Sportwagon. 6-speed, of course.
Okay, laugh at me for this one if you want, but I want an early 90's Civic SiR. It's like Lego for adults, you can build a really neat and fun car to take to a track and have a ton of fun. I worked for a Honda dealership when I was 16 and drove lots of different cars, but the Civics were so much fun to just pound on and they wouldn't break.
I'd also like to have a few bikes.
86-88 Yamaha RZ350R. Two-stroke blue smoke ring zing wheelie machine.
86-87 Honda VFR750. V4
97 Honda CBR900RR Fireblade.
Ducati 748
If I have any money left after that, I would just keep my eyes open for other things that catch my eye. I love going to car shows and seeing what other people come up with. I don't care about having something fancy to show off with, I find more enjoyment in the connection with the vehicle.