He has a Wireguard VPN to Germany. That hides his location. I used the same exact setup when I worked remotely and it was flawless. But at some point he was connected to the internet without a VPN or his computer would not have auto-updated to the new timezone.
but you need a specific signed letter to get the approval from the embassy to be able to use a foreign insurance policy. And that letter is so difficult to get that 99.9% of people have to get the Thai insurance to apply for the non-OA visa from the embassy. Perhaps you can get that letter again for your new year of insurance and that might help you enter and get a fresh year stamp.
You're making a hell of a lot of assumptions. Where did he say his "friend" was never warned in the past? Perhaps he had plenty of warning and ignored it. Where did it say he was sent back to Canada? He just said he is in Canada now.
Can you go into the BIOS settings and change the time? It's very rare that an IT organization would have locked the BIOS settings, and you can get into those before windows even loads. The computer time should be set in there as well and you might be able to change it.
Normally it would need to be one of the approved policies with from the list of Thai companies. But you say the policy worked to enter originally back in 2024, so it might work again now? The immigration officers are likely not experts at checking insurance policies, so it's hard to say.
because you're not required to have money in a Thai bank. You're required to have money in A bank. When you get to Thailand and want to apply for the extension at immigration is when you need to show money in a Thai bank.