Could you please describe free-est elections that would resolve no, and the unfree-est elections that would resolve yes.

That's up to the poll

MAGA factions nation-wide are attempting to throw out any non-MAGA election officials.

https://www.nytimes.com/2024/06/06/us/politics/nevada-election-clerk-trump.html?pgtype=Article&action=click&module=RelatedLinks

I wouldn't be too surprised if some counties succeed and commit election fraud.. and there's tons of other possibilities with Trump in power

Trump can't run again (and would probably be too old to try anyway), and I don't think he'd care enough about the party to try to damage democracy for it

The current order that promotes fair-ish elections is the same one that says he can't run again. If he successfully destroys that, he can totally run again, or not even need to run.