What Thailand really says about digital nomads and tourist visas
I've been in Thailand for most of the past 15 years, so I've seen all the visa rules since when we would go to the Mae Sai border every single month on the old fashioned visa run, no questions asked.
I also spent much of it on a computer, for investing, keeping UK outfits going and running this blog before even Facebook or Twitter were an option.
Consistently over the years working on a tourist visa is not allowed, and that working is pretty much defined as spending energy.
However there've been multiple public meetings I have personally been to led by Chiang Mai Immigration, and the person in charge of working permits, saying that using a computer for remote activities is fine by them and not considered work, just don't do any business directly in Thailand or for Thai customers.
This apparent inconsistency is little understood, but explainable when you look at how the two different cultures work legally. In the West the law is the law (for the majority of us not above it) to such an extent that a badly phrased law generates loopholes that can only be stopped by a precendent setting judgement in court, or a change to the law. In Asia however the law is generally complaint based rather than universally enforced. And in fact this is pretty international when it comes to immigrants working. In Phuket for example there are a lot of local wealthy businesses that don't want even a hint of competition, and don't benefit much from digital nomads staying versus wealthy high spending tourists. The immigration head there is clear: even putting ads on YouTube while in Thailand is not ok by him.
In Chiang Mai however they are making a lot of money out of us, I have volunteered the money for 5 Thai people full time and some part time for 15 years, without even running a Thai business where that would be required. That doesn't change the law, but I think it changes the interpretation, because basically no one is going to be complaining about that, and I am not competing with anyone in anything I do. I have little to do myself anyway when it costs 5 baht where I'm staying to fix the brakes of my motorbike.
Summary: It seems, to date, ok to be on the internet remotely in Chiang Mai, so long as not annoying or confusing any Thai national for any reason whatsoever even if unjustified, as that is the kind of thing that may have led to the immigration raid on PunSpace a while ago. I recommend keeping a distance inside where you think the law is for additional safety. It's no big deal, the worst that can happen is we have to be based in a location like below, and just come back to visit our favourite city.