My understanding is that if you want to start the process for a retirement visa, you should have at least 30 days left on your last stamp. Since you’re stamped for
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, you will either need to initiate the process in the next few days or get the 30 day extension to Feb 17 to give yourself more time. I think it’s smart to obtain the long term visa as you risk denial of entry if you are stringing a lot of exemptions and extensions together.
if a person strings together multiple consecutive visa exempt stays in Thailand, immigration starts to pay attention and might deny entry or give a warning to get some type of long stay visa. On the other hand if visa exempt stays in Thailand are separated by stays of reasonable duration in other countries, then you should be fine. In this latter example, you are functioning as a tourist, not someone who is trying to stay long-term in Thailand on short term visa exemptions and extensions.