we've done it twice. Takes a bit of work but I enjoy the challenge. Don't recommend it for most people though. Only with Thai Airlines. Air Asia, Philippine Airlines and Cebu Air no you will never get a waiver with them.
My wife flies with me and without me no CFO sticker in her passport. Never been asked. Sometimes one way and sometimes with a return. Usually just sign a waiver if required. Occasionally we just waste the $100 return ticket. As long as you have a flight out of Thailand within 30 days the airline doesn't care. Cheap flights to Saigon or Kuala Lumpur is easiest. The Philippines immigration are mostly unprofessional idiots who love to intimidate their citizens upon departure. Why? Mostly jealousy and incompetence. Though the odd one is very pleasant. Stand your ground with them and ask for a supervisor if necessary. Doesn't matter if you are married to a foreigner if you are going through immigration. Different lines exiting Philippines and most Asian countries you will be treated just like anyone else. Best to have a visa but not necessary if you have a return ticket in that 30 day window. Easy.
On a Canadian passport. Ridiculous. If they insist sign a waiver. If you need to buy a ticket go online and buy a cheap one out of Bangkok to Kuala Lumpur or Vietnam is usually the cheapest. What airline did this to you. Nonsense, you should get a refund.
that can be where you will have a problem. Maybe. You shouldn't have a problem entering Thailand. They will stamp you in for 30 days without a visa. Usually don't ask anything else. Leaving the Philippines is so annoying we hardly ever go back. Very annoying immigration.
Robert is correct as usual. Where are you flying from as if it's the Philippines you might have a problem with the airline and/or immigration. Especially you. Better to get the visa, or change the return to 30 days. You can also sign a waiver with the airline if they insist.