Overall, this is a very simply process, but people seem to love making things more difficult than necessary.
First, if you qualify for LTR, this is the no brainer move. Best visa Thailand has ever offered. If you qualify, it’s easy. If you don’t qualify, things are a bit harder. But not much.
You can get your retirement either in Canada before departure (health care insurance required) or after arriving in Thailand (no insurance requirement). If you have a pension exceeding 65k baht monthly, embassy will issue a letter of affidavit and no need to deposit 800k in Thailand bank. Which is foolish anyway.
Check with CRA about your intent to establish non-residency with Thailand.
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CRA can be very helpful, and no need to waste money on a tax consultant living in Canada with minimal experience.
If federal govt employee, simply switch to comprehensive coverage and you are fully covered in Thailand. If not, you will want to get local medical insurance IN Thailand after arrival.
We have been here since before COVID, and it’s pretty amazing overall. A serious life upgrade over life in Canada. Enjoy the transition