Fuck there are some sad little people in these FB groups who take any question no matter how logical or innocent to be an excuse to shit on others.
I think the question is perfectly valid, and if you’re arriving at 11:35PM then you really should be getting that extra day because you’re entitled to 60 days not 59 days and 25 minutes.
I think you’ll be fine to drag your feet Jack, take your time getting off the plane, stop at the toilet if you need to, and hopefully it just naturally happens that you cross after midnight.
I have two passports, and I opened a bank account in Thailand with one of them many years ago but stopped using that passport as it was older and more worn out.
Years later and I have mostly used my second passport since then, and when I tried to go into Bangkok Bank on my last visit to Thailand they wouldn’t serve me unless I was stamped into Thailand on the passport I opened the bank account with.
(Stupid policy considering I had both passports with all necessary stamps and proof of ID/Blue Book etc but that’s another story lol)
So naturally on my next visit I tried to use my first passport to enter so I could access my account, and I was immediately flagged, dragged into a room, and threatened with deportation for what they perceived as me trying to do exactly what you just said.
Even after explaining that my only intention was to be able to access my bank account, they refused to recognise my first passport and only stamped me in on my second passport.
Moral of the story, having two passports doesn’t matter, your fingerprints and your face are the same and you’ll get flagged.