"It will be happening about 2 months before I get a 2nd (gov) pension that will then take me over the required income level for a 'retirement' visa"
Expensive is superior to unavailable.
I believe once your work permit ends so does your right to live in Thailand or at best you are given very limited time to make arrangements. From what I read you must leave the country and apply for a visa to return. You can do border bounce twice and get 4 months if you extend each visa.
My Canadian pension was to have kicked in June 2022, I am still waiting to see a dime but am assured it will be paid retroactive.
Without a plan B one can find themselves in a very deep hole not of their own making.
I have a 22 year old daughter that struggles with low wages and high rent in Canada. My wife has been given a home, a car, a university education and years of support when I worked in Canada and to be very honest and cold hearted I leave the vast majority of my limited funds in Canada. When something happens to me, my children will get their share with ease and the funds in my bank account in Thailand will be negligible. What is in the joint account is hers.
25,000 baht a year is a price I am happily willing to pay to keep the 400,000 out of Thailand.