"Baba Yaga and her 52 apprentices"? That's possible, but I'm not actually sure how this can become a battle because the obvious move is for Riddle to "bombarda" his own skull.
I'm thinking we are going to get some more talking. And it is pretty likely we are about to have explained to us how he already lost...
Wait. Are we at all sure the Tom's are still outside the mirror? If the plan was to trap Voldemort in the mirror, how do we know that didn't already happen, and this is years later when they finally finished tracking down the horcruxes? Because the best mirror-plane prison would be one with no passage of time in it.
This also fits the prophecy, because in this case, Harry did defeat him, by being willing to go down with him. Which is a power he knows not.
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It might be worth considering a mixed or hybrid path -- if you can get a high-paying traditional (software, finance, etc.) job, while being very frugal and saving money (and you don't have much or any debt), you can get pretty quickly to the point of having a very comfortable savings buffer. If at that point you use your savings for living frugally, but not for funding your startups (do that with Other People's Money), I think you'll have more runway and more options than you might otherwise, and should you find that the startup life is not working out you should have a good backup trajectory available where you go back to a high-paying traditional career and retire.
I'm curious why you think (4) seems unlikely -- is this a fact about your personality, or about the world (i.e. you think there will be no normal-ish jobs, and/or the world will not survive to see your retirement?) Considering again high-paying jobs like software and finance, I think the math shows that a very frugal person can effectively retire after very few years in such a job -- perhaps as little as a decade, certainly as little as two, which is similar to your stated startup timeframe -- depending on what your goals are. And once you're in "effective retirement" (i.e. you don't have a problem supporting yourself), then you're in a great position to try to get a startup going.