As many times as you want until an immigration officer says no. Also, staying out of the kingdom for a while will help you immensely between border runs.
so many borders that have way more people bouncing in and out but they chose these 2 rather secluded borders. Its madness. Would love to find out what is actually going on, these sort of things happening only at 2 borders are just madness. Oh, one more thing, after the 15th of July, an officer in Central Plaza Chiang Rai told me that extensions now are unlimited, one just needed to pay 1900 to extend every month with 'no limits' (those are his exact words). He said it rather loudly at the counter and everyone heard him. Fast forward to last night, my friend called the Central Plaza Immigration and he was told only 1 extension after coming in from another country. Have you heard of such a thing as unlimited extensions after the 15th of July?
thats crazy. Most probably said that to scare both of them, or everyone passing that border for that matter. And I was also surprised they were asked to show onwards plane tickets, its rare for land borders, at least in my experience.
2 friends just came in back today after staying for 2 nights and they were asked to show plane tickets as proof of when they will leave thailand. They had to buy the cheapest flight tickets (to Penang for 3000+ baht) and they were let thru. One had used up all his land border crossings per year + extensions, the other one only border ran twice (including this time and 1 extension this year. One is from Singapore and the other French. Huay Xai - Chiang Khong border.
I can confirm this as I just talked to the officers in the Chiang Rai Immigration Office at Central Plaza. In fact when I was translating for my friend he told me without being asked that border runs now are unlimited. You have the option of paying 1900 for extension or do a border run if you are near a border. No more twice a calendar year bs, all started from the 15th of July. And before a smartass comes in and tells me all this is valid until an officer at the border informs you that this will be the last time you come into the kingdom this way, yeah, even my 5 year old neighbour's daughter knows this. My advice is this, enjoy it while you can, because thailand is thailand.