I’d say that as long as you enter the endeavor with the understanding that there is the possibility that might not make money, that’s fine. Just like with stocks, bonds, real estate, etc, investing in cars involves risk. With cars though, consideration needs to be taken to the extra costs involved of maintenance (even if they’re sitting they should be kept up and detailed), storage costs (rental, heat, power, etc.) and insurance. I’m not saying don’t invest in cars, just approach it as well educated as you can (but I think you’re doing that since you started the thread in the first place).
Keeping all that in mind, the absolute worst investment anyone can make is buying a car you do not like or enjoy. That way if you break even or lose a couple grand, you still owned a car you got a kick out of. You should also consider that even if the plan is to store it, it should still be exercised periodically to keep the engine lubed, keep seals from drying out, and so on. So if a Skyline doesn’t scratch that itch for a fin car, I’d widen your scope. If it does, then jump on it!