My take, for what it is worth! - from what we saw in the movie

Batista too ”seems to be in the dark about how well the rebels are doing” Batista gave assurance that according to his staff the rebels will be driven out of the city before the New Year!

Sure thing Woltz Michael arranged the below which just one phone call to the Hotel Concierge and voila! everything in place
1. his own driver to take him to the airport
2. plane and a pilot

Michael also knew a place Fredo and Michael can spend some time together

Nobody could have predicted Batista's resignation that night, New Year's Eve which resulted in the “country crumbling around them”

So, I don't think it is about Michael “trusted the pilot enough to stand fast” irrespective....
I believe, the pilot would have been just a regular commercial pilot, may not even know who his passenger/s are [arranged by the Hotel Concierge] and perhaps blissfully unaware of all the rebel uprising chaos, standing by at the Airport

As regards “Michael seems to know Roth's exact plan” for Michael's New Year's Eve assassination If my memory serves me right -
Turnbull had a credible theory that Michael would have twigged straight away as to why Michael needed to be escorted in a military car for his protection
[when according to Roth “This county's had rebels for the last fifty years It's in their blood” and it is business as usual]

Whilst Michael would among others “staking his life" seems implausible to me as well but seemingly that's what Michael did!

I don't think Michael thought “killing Roth will end the [Michael's assassination] threat” nor Batista was even a consideration for Michael because I believe Michael would not want Roth or Ola's bodies found until Michael was out of Cuba not because I believe Michael could be linked to the deaths but to avoid the hassle, delay and Michael having to play the grieving son!

I am not sure Turnbull "Michael also was confident that Roth still thought Michael believed that Pentangeli was behind the shooting and that their relationship was still good"

I believe the charade was finally exposed with Michael's “Who had Frank Pentangeli killed?” Roth's soliloquy and Ola looking smug that Michael has no idea Pentangeli is alive, Michael is no match for Roth