Well, that’s exactly how it works, and no — the insurance date printed on the visa is not the operative factor at entry. Immigration routinely asks for updated proof of health insurance when stamping in on a Non O-A. Plenty of people renew their policies after obtaining the visa, which is why the original expiry date on the sticker is irrelevant in practice. If her insurance had been renewed, she would have been stamped in until the new policy’s expiry until November — not merely June/July. So let’s not pretend that carrying proof “isn’t needed.” It very much is, unless one enjoys unnecessary complications at the counter.
It is a multiple-entry visa with the right to re-enter still embedded in the visa itself during its validity period. However, it is correct that you will need a re-entry permit for the second year.
That is precisely how a Non O-A visa operates. You are admitted for one year at a time as long as the visa itself remains valid, or until your health-insurance policy expires — whichever occurs first. The 90-day report is entirely unrelated to entry regulations; it is simply an administrative reporting obligation triggered once you have physically remained in Thailand for 90 consecutive days.
For entry, the required documents are straightforward: your passport, your Non O-A visa, valid health-insurance coverage, and a completed TDAC electronic arrival card.
The timeframe varies by location. Some bigger immigration offices like Bangkok, Chiang Mai, and Phuket allow 45 days before the due date, while the rest are 30 days. Using an agent doesn't typically change the timeframe.
Reports indicate that the DTV process in Ho Chi Minh City is quite straightforward, with visas being approved within a few days or a little over a week. The announced processing time is only five working days.
You should not have any problem at all with immigration based on the travel pattern you’ve described. You completed a full 60-day visa exemption, took a 30-day extension, and then left Thailand for more than four months while staying in Vietnam and the Philippines. That is a genuine and substantial absence, and it places you completely outside the scope of the new guidelines, which only target consecutive border bounces used to prolong a continuous stay. You have not overstayed, you have not tried to maximise back-to-back entries, and you have been out of Thailand far longer than the duration of your previous stay. In other words, you clearly fall into the category of a normal tourist. As always, the final decision rests with the immigration officer, but there is nothing in the current regulations or practice that suggests your entry would be problematic. Just make sure you carry an onward ticket within 60 days.
It's essentially the same visa, just different qualification paths. As a remote worker, you'll need to prove your employment, and for soft power, you'll need to prove participation in an approved soft power program.