I went with my son earlier this year. To my horror before we left he told me his passport expired in 3 months, couldn’t get an appointment for a new one, took the chance and immigration never mentioned it.
Always better to be safe than sorry but if you have a flight home before it gets close to running out you will probably be ok.
As the others have said, get through before midnight, once you are airside I believe you have technically left as you can’t come back through without an escort. So I think you would be good to go.
why do you need to do a border bounce every 180 days, I believe you can extend for 180 days on each visit so a border bounce is only requires every 360 days 🤷♂️
That is definitely workable and how I would do it if I didn’t have a dtv but it looks like the 60 day will be reduced to 30 days so you may only get 5 months this way by the time the first 90 days is done it could be changed. Who knows 🤷♂️