It's also possible to get a multi-entry Non-O, which would mean he could just leave the once, without having to worry about 60+30 extensions on the METV but that may not be cost-effective in terms of fees.
I spend 6 months in Thailand (in two blocks of 90 days) and 6 months in UK, each year. I've tried a variety of visas over the years but the easiest is now the non imm-O based on being over 50 with pension. Only significant requirement is to show pension statements, no proof of insurance is now required.
In fairness, this was the first time I'd used the Airport office. Previously, I'd always used Promenada, in CM, which never asked. Nor did the Phuket office last time.
Good question. Still hypothetical for me at the moment. Last time I got an O-A, I just squeaked in before any insurance requirement was imposed. The Emirates policy was certainly good enough to get my present sandbox COE, albeit with a visa exemption.
Understood but you will have to purchase insurance for the extended portion, if you want it. Unwise to have no insurance. Personally, I would book my flight presuming an extension and take my chances.