one could always get a work permit, while being married to a Thai and on a Visa based on this marriage. You cannot get one if your visa/EOS is based on retirement , though
seeing that Justin is neither English nor US, maybe his embassy is issueing a legalized proof of YEARLY income letter, which he can use as financial proof when applying for the Extension of Stay. He should ask his Embassy
So Justin would theoretically be able to stretch his admitted stay until November 26th in case he needed to collect 12 months proof of income or deposit 400,000 THB in his bank account for two months, before applying for the 1-year Extension of Stay based on marriage
If you can prove your marriage to a Thai, you can apply for the 60 days extension based on visiting family once every calendar year. Justin's 60 days would start on September 27
unfortunately, Immigration cannot transfer a visa sticker from the old into the new passport. They only can transfer the "admitted until" stamp. You will have to keep your old passport with you until a new stamp or extension is given
However you see, what that kind officer said is not shared by his colleagues. So plan B is still open: Elite Visa. It is a one-of-a-time emregency, you can go back to Non-Imm-O or O/A before the 5 years (can get 6 years,actually) are over. Elite means a "parking fee" of 190 Euros per month - how much rent do you pay making Thailand still an inexpensive location?