I'm not quite sure what you mean but it wasn't a planned trip. It was an emergency and I bought the tickets 2 nights before leaving with enough time for a covid test and a last minute trip to immigration to renew my extension and get a re-entry permit. I knew I had to be finished with quarantine and back in CM by July 19.
Yes. I told them I was flying out of Chiang Mai to Bangkok later that afternoon and then to the US that night. But I wasn't planning to stay longer than a month and if I had to, I would have come back with a tourist visa or applied for a new non-O based on Thai family. They weren't mean about it, but that's just how it was. They assured me I could get a COE with an under consideration stamp which I was worried about.
From my experience (4 years of extensions for non-O based on marriage to a Thai) in Chiang Mai, you will be asked to come back 1 month after your extension expires regardless of how early you applied. So for the past 4 years, no matter how early I went, my stamp said to come back July 19- a month after the expiration (June 19th). This year, I applied May 31st and hopped on an airplane that night to head back to the US (family emergency). I asked if they could issue the extension that day and they said absolutely not. They said I had to be back before July 19th which is when my re-entry permit expires. I'm currently back and in quarantine in Bangkok.