Will I have trouble entering Thailand with a history of visa runs?

RadiantPelican9733 Good to note, the Immigration Officers have been instructed to look for those that ABUSE the Visa Free Entries with Extensions to stay longer than the allowed 2 entries 60 days + 2 extensions 😊 Longer than 180 days) In the country, and thankfully, the travel history shared falls way outside those parameters, so you should be totally safe to enter the country without any hassles. Keeping in mind that most interactions with Officers last less than 2 or 3 minutes at best, being organised with your documents is Key, but if you feel the need to make 100% sure there is no hiccups, perhaps dress business casual at the very least and make sure be polite with any interactions with the officers that way you will have covered every base and should be totally clear to go enjoy you stay. I know you mentioned it, but just to reiterate, one thing they like to question is Proof of return, which a return flight definitely satisfies that requirement. Don't forget your 20,000 Baht Cash IN HAND (Showing the money in a bank account on a phone can be cause for a refusal) and have the Air BnB booking handy in case they ask and you are as good as gold. Safe travels and try to be good 👍