there are really only two paths a car guy could take after winning the lottery.

1. open up an auto museum to the public and hire some people to run it so that you can get cheaper insurance for your collection, make money on it, and have it all serviced/maintained on company dime

2. move within 20 minutes of a mid-tier race track and start with a FWD 4banger and upgrade the car and then replace it with a better car as if you were playing IRL gran turismo