I want to share my story here. I'm Canadian.
In my passport I have several exeption visa( the one you got for free when you arrive ) from 2016 and 2017 and 2 tourist visa from visa run done in 2108. In 2019 I've got 2 exemptions , one when I arrived from Canada and another one from a little visa run in Cambodia. Both went well I had nothing to show. Nothing.
But I just came back from the Philippines and They asked me for a returning ticket and money. I showed them but still this was not enough. The guy insisted that I need to apply for a tourist visa from my country. After some negociation, they let let me in with no warning in my passport. I had the normal stamp for visa exemption, 30 days that I plan to extend.
That it, so I will just apply for tourist next time loll. I will not take this chance anymore.
TLDR : Answer Summary
A Canadian traveler shares experiences regarding entering Thailand with multiple visa exemptions and the challenges of being admitted without a formal tourist visa. Despite having prior exemptions and successful entries, the traveler faced scrutiny upon returning from the Philippines, leading to the decision to apply for a tourist visa next time to avoid complications. Comments from the community suggest that obtaining a valid tourist visa beforehand could simplify future entries and ensure compliance with immigration requirements.