I am on an extension of stay based on retirement and am coming back to the Kingdom later this month. (I have a reentry permit)
Do I need to have 20000 thb or equivalent under these circumstances?
Answer summary
If you are re-entering Thailand with a retirement-based Extension of Stay and a reentry permit, it is unlikely you will be asked to show proof of having 20,000 THB in cash upon arrival. However, it is advisable to carry it for peace of mind, as while some travelers might not be asked for cash, having it can help avoid potential issues.
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As you have an Extension of Stay as retired and a reentry permit to re-enter Thailand...
It's not likely that you will be asked by Thai Immigration officer who greets you to show PROOF of your having 20,000 Thai baht or its equivalent CASH upon Arrival.
I always carry it with me when I enter Thailand... BUT use your OWN judgement.