Is 5 weeks enough time to apply for a one-year extension of my retirement visa in Thailand?

I believe that the OP has the answers needed for his question.

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If you are staying for only 5 weeks, it wouldn't be enough to apply for a 1-year extension, unfortunately. But if you are going to be back in Thailand within the first 90 days, you can re-enter on the same stamp with a re-entry permit that you will get before you leave Thailand after 5 weeks, and continue your procedure for a 1-year extension.

When you enter Thailand on that visa, you will be stamped for 90 days (until around late June or early July) on the arrival day as Day 1.

1. You immediately get a bank account in Thailand to transfer your funds internationally. And go to the local office to get the latest handout for requirements for an extension based on being over 50.

(extra -1: get a re-entry permit before you leave Thailand.

extra-2: return to Thailand on re-entry permit within the first 90 days, before the end of June)

2. When your funds are in your bank account for two months or more AND your stamp remains less than 30 days (45 days in some provinces such as Bangkok, Chiang Mai, and Phuket) you go to the local immigration office to apply for a 1-year extension.

3. Get the lease or whatever document for your address in Thailand before you apply for an extension.

This is general information for an extension based on being over 50. You may need more documents at your local office.