I doubt that anyone knows the answer to those questions right now.
The answers also depend somewhat on what we mean by "convicted." A person who is convicted in a trial may still win on appeal, and a conviction isn't final in any real sense until all appeals are exhausted. For example, Elizabeth Holmes was indicted on June 15, 2018 but she was not incarcerated until May 30, 2023. Trump's lawyers would undoubtedly be able to delay his incarceration for much longer.
Having said that, here are my highly speculative best guesses.
If he's convicted on all 37 counts I highly doubt he'd walk away with a fine. I haven't reviewed the federal sentencing guidelines for these crimes, but I'd be shocked if a fine is within the guidelines, and I have a hard time seeing the courts deviating wildly (again, we're assuming conviction on all 37 counts).
Assuming he's sentenced to incarceration, exactly what this would entail is (in my opinion) very unclear. Realistically, throwing him into an existing (unmodified) Federal Prison would create numerous problems (e.g. another prisoner puts a knife to his throat and says "Tell me the nuke codes!"). My best guess is that an existing facility would be heavily modified to provide security (and something akin to a country club environment). He wouldn't be hopping on his jet, though.
With regards to him being barred from any political movement, the court doesn't have the power to bar him from future office because it is not one of the potential consequences defined in the laws he's been charged with. In theory, the disqualification clause could be invoked, but it would require a separate legal action and no one really knows how it would be implemented.
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Could the disqualification clause prevent Donald Trump from running for president in 2024?
Theoretically, yes. Section 3 of the Fourteenth Amendment gives Congress the power to disqualify someone who has already held a public office from holding "any office" if they participate in an "insurrection or rebellion" against the United States.
But since this mechanism has never been used against a president, there are still questions to resolve [editorial comment: this is the understatement of the century!]. The disqualification clause applies to current and former federal officials, state officials, and military officials. However, legal scholars are split on whether the disqualification clause applies to the presidency.<<<
Section 3 of the Fourteenth Amendment was originally intended to keep former Confederate officials from gaining power in the reconstructed government following the Civil War. Known as the "disqualification clause," this section was fairly obscure until January 6, 2021, when supporters of...
constitution.findlaw.com
I strongly suspect that the trial in the Florida case will drag out well past the 2024 election. I can't imagine that the disqualification clause would be invoked in a separate legal action before the Florida case has concluded (an acquital is outside the proposed hypothetical, but in the real world this possibility would make disqualification much less likely if the trial is ongoing)(in my estimation the odds of disqualification before the trial is concluded are effectively zero).
What would happen if Trump were to win the election while the Florida case was still in the trial phase? I really don't know, but it would be a huge mess. I suspect (I'm really guessing on this one) Trump would attempt to pardon himself, and the trial would be put on hold while this issue was decided in the courts.
Even if Trump were to be convicted on all 37 counts, his lawyers would undoubtedly file appeal after appeal to delay incarceration, and many of the appeals would probably go all the way to the Supreme Court. As noted above, Elizabeth Holmes delayed it 5 years. A SWAG is that Trump could delay at least 10 years.
Odds are pretty decent that he'd die from natural causes before all of the legal proceedings were exhausted. Again, that's just a guess. I really don't know.
