I don't think I can answer this one.
I've never been in a position to be able to participate in all tiers of collecting, not in cards, or any of my other hobbies.
But when I first really got into cards, I was probably pretty close. The only one that was truly out of reach was the Wagner, and maybe Plank.
But I've always been more of an opportunistic collector. It was rarely "what card can I afford?" more like "what card can I afford with what I have on me right now?" And even then.... I've occasionally passed on cards I wanted because of timing. Like a Drum back T206 at $200, because I'd only brought about 225-250 to the show. Came to my senses an aisle later and went back but it was gone.
And the cards I passed up that I could have rounded up the money for back when I started...
But the opportunist in me has been lucky a few times, so I can't complain too much.