It is always up to the Immigration Officer. Lucky that your wife was there to assist you. While the 2 x per year is o longer and in theory there is no limit to the number of entrys, the Visa Exempt stamp is only for tourists. As you have ha Thai wife and are in Thailand making regular weekend trips, it would be reasonable for the Immigration Officer to decide that you are no longer a tourist and deny you entry into Thailand. To enjoy regulular safe entry you need to get a long teerm visa appropriate to the reason for your stays.
Hoops? Need acceptable photos, need proof of marriage from Government office, wife has to go to Immigration with you, visit to your home by Immigration police and need a neighbour to speak on your behalf, do not get the visa on the day: Retirement does ot need any of those. And you did not get in less that an hour. You had to go back 14 days later to get it.
Mike Dias. If you arrive on a Visa Exempt stamp you would not be able to open a bank account in Thailand and yuou meed a bank account to apply for a marriage visa. Best to obtain a long term visa from your home country.
If you mean that you have a Extension of Stay based on being over 50 and you have a reentry permit and you will be returning to Thailand before your extension expires, then you will not have a problem. When you enter Thailand, just bring your old and your new passporsts.
You are not getting an extension. Your are arriving without a visa (or extension) and expecting to get a "Visa Exempt" stamp which is intended for tourist who visit Thailand for a short stay (usually interpreted as 90 days or less. Based on your history of visits to Thailand, Immigration could rightly decide that you are no longer a tourist and refuse to give you the stamkp, effectively denying you entry. If you want to spend more time inThailand without being denied entry you need to get a visa.
It sounds like you have a solid history of visiting Thailand using the Visa Exempt entry. If so, Immigration may consider that you are abusing the system which is intended for sshort term tourism. You may get denied entry unless you arrive with a long term visa suited to the reson for staying in Thailand.