if you go for stuff that wasn't winning/famous at the time, the costs come way down. although since everything was bespoke, replacement parts are often complicated.
i have a '60s lotus 23, which was built for Le Mans, and it was very low six figures. but an engine rebuild is $30k...
Are track days the only viable place to find/meet these people who can help maintain such cars, or there are other ways. I couldn't hold back the question, but feel free to ignore
For stuff like that, best to go to the vintage and historic races and events. I explicitly looked for cars that were eligible for the Monterey historics (I have two currently.) It helps to find people who specialize in the vehicle you have, as well.
Trackdays skew towards much more modern cars. Although I met the shop that takes care of my stuff at one (they did Spec Miata rental, and now I race that too)
i have a '60s lotus 23, which was built for Le Mans, and it was very low six figures. but an engine rebuild is $30k...