Can I fly in and out of Thailand after a year of visa exemptions?

Here's my opinion:

1. You need to leave tomorrow, to avoid being on overstay.

2. When you return to Singapore:

a. Identify what type of Non-O "retirement visa" you want. There are many.

b. Once you identfied the visa you want, apply for it. The Singapore system is online, and also allows people who are NOT from Singapore to use the system. See for more information about how to apply.

3. If you want the visa from inside Thailand, re-enter Thailand by land, and apply at your local immigration office. You can enter twice, by land, and on each entry you get 30 days, which can be extended by another 30. Chose the border carefully.

you can apply for a "conversion" from an exempt entry to a 90-days Single Entry Non-Imm-O based on being over 50, on Immigration Office inside Thailand. In the last 30 days you can apply for the 1-year extension of Stay based on being over 50, if you meet all requirements (financial & TM30, documents etc) All on the assumption you are a Canadian with a Canadian passport who just happens to reside in Singapur. You could ask, however, the Thai Embassy in Singapore if you can apply for a Non-Imm-O with them, maybe your "resident" documentation will be accepted

No...your history is yours. However you are allowed two land border entries per calendar year. Each gives you 30 days to most people. Which can be extended 30 days at Thai Immigration 1,900 Thai baht fee each time.

>" Is it OK to fly out and in again."

No, the "two entries without a visa" reset only for land entries, not air. You can try flying in, but you run the risk of rejection.

>" Does a new calendar year wipe out last years visa exempts."

Only by land. When you say you are a "Singapore resident", does that mean you're a citizen with a passport?