What options does my retired friend from Canada have to stay in Thailand for five months?

@Ken *******

get an Non O for 90 days from his local Thai Embassy before he leaves Canada, this can be done online and he no longer needs to mail the passport. He'll get 90 days stamped in on arrival. In Thailand, with 30-45 days left on the entry stamp go to the Canadian Embassy or consulate and get the affidavit mentioned by Philip, just needs to provide his Proof of Income from CRA. Then go to immigration and get the year extension based on retirement. Once he is ready to head back and sell everything, he can easily get a re-entry permit at the local immigration or at Suvarnabhumi airport when he departs. We did this last fall and it's super easy. The Thai Consulate in Vancouver was really helpful in answering questions and the overall process. The Canadian Consulate in Chiang Mai was great to deal with in getter the affidavit.

If he’s retired once he gets here he’ll probably want to stay longer. Have him apply for an extension based on retirement. If he makes more than 65 K Bhat a month he can get a verification letter from the Canadian Embassy. It can be done by email. $50.00 cad. The extension will cost him 1900 Bhat. Very easy to do. I came here for 3 months two and a half years ago. That’s what I did.

A bit of overkill but he could look at getting a non OA visa which would give him a year on entry, but quite heavy conditions on getting that including mandatory health insurance. Tourist visa and border bounce probably the best option.

There's the STV if they are still in their home country to get it. But conditions are onerous!

Your friend could get a tourist visa which would give them 60 days on entry and can extend for a further 30. They could then pop over to a neighbouring country and come back on a visa exempt stamp for 30+30. That would cover the 5 months.