How long do we need to be away (third country, not “home”) between 60-day exemptions?

I am a solo mom with two kids, all American passports on a 60 day exemption, which is up on the 26th of Dec. I intend to get a DTV as a digital nomad, but wanted to see how it is before going through the whole process, as this is our first time in Thailand.

My rough plan is to be in Taipei for Feb/ March, and apply for Thai DTV from there. In the meanwhile, we’ll be going to Malaysia over winter break and planning to return Jan 1. We won’t be there long enough to wait for the DTV to go through, so we’d be returning for another exemption. Is 8 days long enough they would be okay with another exemption? Or would they be okay with it because it would be only our second entry?

Alternately we could stay in Thailand over break and apply for an extension but I don’t know how likely it could be refused, or if the 30 days starts the day we apply, or if it gets added to our original date.

My kids dtv visas didn’t finish until after our travel dates (mind you I started this processing 3 months before our planned journey) but the embassy (DC) kept taking 3 to 4 weeks to ask for more documents, by this time our flights had come. I entered on DTV my kids on visa exempt, 2 weeks after arrival they have sent their evisa dtvs.

My question is, can we go across the land border to Cambodia, stamp out but on entry stamp in under the dtv with one of these border run agencies? Or does anyone know a driver who can get take me and kids (total 6 people) to do this?

Thank you very much.

And for everyone who says I should have waited for their visa to come first, you are more than to keep scrolling.

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