I don't think Trump has the interest of literally any of his voters at heart. He's only interested in helping himself and he legally can't even vote for himself.
Edit: TIL Trump can still vote.
Florida (Trump's home state) Law:
a felony conviction in another state makes a person ineligible to vote in Florida only if the conviction would make the person ineligible to vote in the state where the person was convicted.
New York (State of felony convictions) Law:
a person convicted of a felony is disenfranchised only while incarcerated for that felony.
Should be noted that young male voters are some of the least reliable voters to turn out. Yes, he's gone hard on the Joe Rogan demographic with his pandering. Yes, its working (because... advertising works!) No, I don't think its going to be a winning strategy in the end, because them hoes ain't loyal.
Unfortunately that was just wishful thinking. I had to confirm and according to Florida and New York state law, he will be about to vote unless he ends up being incarcerated in New York at the time.
It's hard for imprisoned people to have a fair vote, unhindered by pressure from guards, administration, or gangs. You think for-profit prisons selling slave labor of their inmates is bad, just offer them the opportunity to sell their votes.