Turn my work at home life into a digital nomad life in Thailand?

Hello everyone,
I'm Farid, I live in Chile (Spanish speaker but English fluent). I have been in Thailand several times (and other Asian countries) and there is something unique in the Asian culture that I really like. I know Thailand has its pros and cons as a nation, but beyond its known appealing qualities, one of the most interesting for me is that this one of the cheapest countries to live in.
I'm working from home for my main job in my hometown. Under normal conditions, I have this and other 3 part-time activities that are face-to-face (teaching and touring), now suspended because of the pandemic (but possible restarting online soon). The bad news, of course, is the lower payment, just enough to pay my rent and living expenses (that's equivalent to around THB 25,000). The "good" news, assuming a long-term "work at home" system, is the possibility to turn my current (and future) online salary as enough income to "live" in Thailand.
A bit of context: my main job doesn't require a mandatory presence in the office. There are some meetings, but online presence is acceptable. There are some telephone calls, but a Skype number could be a solution for incoming and outgoing calls; I don't have a work permit for Thailand but, following the guidelines for Chilean citizens (90-day stay, don't need tourist visa), I could visit a neighboring country for a couple of days, and then re-enter Thailand to comply with the law.
I don't pretend to rely on my current jobs indefinitely (nor pretend an eternal "work from home" system). Instead, I would take advantage of my stay for job seeking in Thailand and try to get a work permit there. I know that a "comfortable" salary to live in Thailand is around THB 35,000-40,000, but I have read some cases being able to handle it with ~25,000. Just for your reference, I'm single, I live alone, let's say I have some experience saving money and I know that rent and food prices are higher in my country.
I know this plan can sound risky and unnecessary, but bear in mind that my whole plan to live abroad is not new. I don't like to live in Chile, and despite many efforts applying for jobs in developed countries from at least 2 years ago, I think Thailand has a unique combination of a comfortable, friendly and civilized population, with low expenses and enough sophistication. I guess that (farang) digital nomads there have a solid and stable struture for their digital work, so it would be great to know from them, or other people with similar ideas, just to figure out how easy or difficult it could be (I know, not being a native English speaker could be one of these natural difficulties).
Thank you in advance for any advice :)

Howdy pardner! Please read the threads posted over the last few months so you will understand that your plan to leave the country every 90 days won't last long! Thai immigration is on a mission to cut down on Foreigners overstaying and they are very good at their jobs! Cambodia is better place for what you're hoping to do! And by far the cheapest place to live in SE Asia and still have enough infrastructure and amenities to seem less third world! Rest assured that Thailand is a developing nation which is about half step above third world!

Hi,
Thank you for your reply. I will take a look to previous posts in regard to the same matter. I would say that this idea came to me because normally Thailand is seen as a great place for digital nomads, but probably many of them are traveling to different places.
Anyway, I know the 90-day re-entry scheme is not ideal but I thought it was not illegal or questionable (as long as you are spending money in the destination country).
Thanks for your advice!

"Digital nomad" is not what you're trying to be, it implies that you keep moving and don't settle down for more than 1-3 months. What you're trying to do sounds more like "an expat who telecommutes". Also, there is a lot of hype and bs around the term "digital nomad" on the internet, it's been a buzzword for the past 7-8 years. Be wary when reading articles about it, too many people trying to make money by selling you the dream, presenting the upsides only, pictures of dude working underneath a palm tree on his laptop while sipping a coconut drink, trying to sell you books with their deep wisdom on the topic, selling you travel/visa/accomodation advices, etc.

Hi, thanks for your reply. Indeed I was trying to find a expression to define my plan and sure, an expat who telecommutes is more accurate. I have seen these "vacation-style" blog posts, but my main motivation is the different culture and low maintenance costs.
I was curious if actually more people is exploring a similar idea because "work from home" could be essentially "work from anywhere", but I know not all countries have the same rules when it comes to entry requirements (and not all companies have the same rules regarding where are you located when doing your job; fortunately, my institution don't have explicit rules about that).

fchar :

fortunately, my institution don't have explicit rules about that

And what about timezone differences..?

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