I had the same question and recently spoke with with a Thai Embassy. They said, their not bothered about the exit date for a visa. However. The airline taking you to Thailand may turn you away at the airport if your itinerary is longer than your visa. It might be advisable to have a flight out before the visa expires... I'm pondering the same situation and nobody knows what will happen at the airport.
Best to drop into immigration and ask exactly what they require. Don't usually need to wait long to ask a question and it seems not all offices ask for exactly the same things.
I've used the multiple entry from Canada many times. I typically get my 60 days which is usually 57 days and a visa extention. I then do an out and in on a land border and receive another 60 days. If your still short do another extension. This is the most expensive option!
they never ask on the Thai end if you have a visa. It's prior to leaving your home country. I've had this problem with Air Canada with an itinerary longer than my visa allows.
even in Hua Hin the air quality can be bad at certain times of the year. With covid wearing a mask was really helpful for me. Never as bad as Chiang Mai and typically short lived.