If you are on a re-entry permit you should be okay. You may need to remind the IO that you don't need insurance if that doesn't work you may have to ask to speak to his/her superior for clarification.
My understanding is that the situation was further clarified to IOs on the 7th of November but it appears that not everyone on the front lines "got the memo".
At the end of the day you just have to roll the dice.
If necessary ask for a 30 day stamp then get it cleared up at your immigration office. I've heard of Bangkok rectifying stamps like this recently.
You shouldn't need insurance because a re-entry permit is based on an existing permission to stay and the insurance is only currently required for new permissions to stay (which includes new extensions).
Having said that, things are all over the place at the moment so they may ask you or they may not.
The alternative would be the single-entry (90 days) Non-Immigrant O visa based on retirement.
You could then extend it for a year at a time. Currently requires that you are over 50 and have 800,000 THB in Thailand in a Thai bank account (or income of 65,000 THB per month being deposited in a Thai bank from abroad).
The other route to this visa is to come in on a tourist visa or visa exempt then convert in-country to the Non-O mentioned above and then finally to extend that.
It's more complicated that way but it may give you as much as six months in-country before your retirement visa begins rather than 3 months.
Trying to use successive 90-day Non-O's from neighbouring countries is possible but not advisable. If you can park the funds then retirement extensions are the best option for you.
Note that you currently need to keep 800,000 in the account for 5 months and 400,000 all year round or you can also use income brought into Thailand from abroad of 65,000 per month or a combination of both.
However, I have heard repeated reports of some immigration offices refusing to allow anything other than the 800,000 method. Talk to you local immigration office if you want to use anything other than the 800,000 deposit method.
Keep an eye on what's happening with the O-A and entries and extensions over the next few months.
It could be that the current implementation is changed to something a little more practical.
in your case the paperwork for a single entry tourist visa will not be dissimilar.
1) Passport Bio Page
2) Recent photograph
3) Declaration
4) Travel booking confirmation
5) Proof of accommodation
6) Financial evidence
7) Confirmation of legal residence
I didn't see (4) on your original list and for (5) just get a letter of invitation and also send a copy of your wife's ID.
As others have said you can use a PDF to create multi-page documents.
If necessary you can use you phone to create them. The Google Drive app will do it for free. The Dropbox and OneDrive apps will also do it (OneDrive you need a subscription for multi-page, Dropbox I don't know).
It seems like you will face some hassle whichever way you go.
Some have suggested just uploading the first page online then taking or sending the full documents with your passport.
This could work because they won't actually check the documents (apart from the automated check of (1) and (2)) until they get your passport.
If you do it this way you must tell them that the documents you submitted online are not complete when you submit your passport.
Chris Po true but as I said, two of the orders make no distinction between new and old visas.
The order regarding extensions, for instance, makes no distinction and people who began extending O-A visas 10 years ago are currently being told that they will require insurance for their next extension.
We don't know if this was the intention or not.
I think that people will have to wait and see what happens over a few months.
Unfortunately as the orders are written you are only meant to be able to get a new visa with insurance from October the 31st.
However a second order says that entries made on an O-A visa after the effective date of the order (October 31st) will require insurance. The second and third orders only talk about effective dates and make no distinction between new and old O-A visas.
We'll see how it works in practice but it may be a while before they are all on the same page. It's highly unlikely that the intention of the order was to force someone with a pre-Oct 31st visa coming back from a weekend in Vientiane to buy insurance.