I've been doing this exact thing for 14 years now. It comes down to who you are, what you do for a living, and especially if you can converse and crack a few jokes in Thai. If you check all the boxes and aren't perceived to be a problem or (potential) burden in Thailand they will happily let you come "forever". Just need 13 more years of this and I can get the retirement visa.
Someone who, for example, works in energy production will have a much better success rate in this than a Pattaya "Bar Manager".