Do you think the elite live better lives in democracies or dictatorships; why or why not?

Better in democracies.
Under democracy, you can buy legislators.
Under dictatorship, you can still kinda do that... But also the state might just take your stuff and have you shot if they feel like it.
That can happen under democracy, too, but elected legislators, generally don't go up against the economic elite, because they're often one and the same, but also because it pays better not to.
- I see it. I don’t have any contact with the American elite, but my ex-wife is married to a Burmese guy and lives with him and our daughter in Myanmar, which is a military dictatorship - and the guy is extremely well off and connected. So I was randomly thinking about this today.

They live better lives regardless of the political system.
- I’m aware but that wasn’t the question.
  
  That would still be my answer, too ;)

In dictatorships they sometimes carelessly fall out of high windows, in "democracies" they sometimes commit suicide with two gunshots to the back of the head.

Look at the international stage and you can see the elite are choosing to live in dictatorships across the board.
They are choosing an environment they would prefer.
I'm tired of pretending like what we think or feel matters in the way things play out.
Join me in getting mad at this.

You don't say which level of elite, so I'm going with a millionaire level.
They live better in Democracies. Better everything: services, amenities, crime, etc.
But they think they live better with more money, which means they think they'll live better in dictatorships.

I'd say the smarter elites would fare better in democracy since there are more options. But it also means arranging the perfect life yourself without burning through all your money.
In dictatorships you can just order people to make your life easy but there are fewer options overall and the people serving you fear for their lives

They're insulated from a lot of the bad things that happen under either form of government, so all they see is a "grass is greener on the other side" situation. They haven't lived under a dictatorship and they think they can influence the transition and running of it to be in their favour, so they push for the change because they think it will make things better for them.
Whether it will or not is entirely dependent on various unspecified factors, some of which may or be outside human control, or even human reckoning without the benefit of foresight.
I'm fairly certain this means that in a world full of dictatorships - and by the gods, we're trying to do that like the silly little idiots we are - the billionaires might well push for a democratic society for exactly the same reason.
But only if they're not in the dictator's inner circle, which is why dictators like to have the rich people on their side.

I think that depends entirely on the democracy or the dictatorship. What matters more is stability and predictability.

Probably dictatorships.
In saudi (technically not a dictatorship, but an autocratic monarchy) corruption is so rampant and widespread that it's not even suprising anymore. The biggest culprits are the royal family, so of course they'd make saudi cushy for criminals like them.
Also, the workers rights here are horrible, fucking SLAVERY is still legal.