Every time you change address, a new Address Registration, Immigration form number 30 or on-line has to be done within 24 hours.

Ask them

@https://www.face*****************

If you apply on-line for the Non Immigrant O visa based on being over 50 years (aka retirement visa) OR for the Non Immigrant O-A (aka retirement visa) or O-X visa (aka retirement visa) , your wife and your son (if he is younger than 20 years) can apply for this type of visa using the same on-line system

@Alan ********

Not see the need to wait two months inside Thailand, just buy the re-entry permit and come back during for the remaining of the 90 days.

But I guess, you looked into that option already, alternative is the Thai Elite Visa.

Two choices:

The METV get 60 days, extension of 30 days and travel abroad

OR

get the Single Entry Non Immigrant visa, get 90 days, apply for the 1 year Extension of Stay and when stamped in passport the Multiple Re-Entry Permit.

the date is mentioned in the Re-Entry stamp and in the big stamp with the text Extension of Stay Permitted to stay xx/xx/xx.

Example where to find the date:

Stll there

As it is well know, some Immigration Offices are more lenient than the other. In your case it seems you always travel into Thailand and stay at the same address, house in your wife's name.

Immigration has that address on file and informs you that you do not need to visit them each and every travel to do this report again.

Be thankful OR if you really wish to follow the letter of the law, go to the website, make an account and make a report within 24 hours after coming home.

Just apply for the visa, you have to hand in your passport so they will notice that you worked in Thailand for longer period.

There is nothing wrong to end a long period of working with a few months sight seeing in Thailand, keep things simple and do not worry to much.

If you already have the visa, apply for the 1 year Extension of Stay using your income if you do not have the money in the bank.