dluek

One good option for you could be Wat Pah Nanachat. Not sure if they help with long-stay visas but I'd guess the abbot would sign off if you stayed there for a month and proved your sincerity. http://www.watpahnanachat.org/

It's the only monastery in Thailand where English is the main language used for teaching and general communication. It's in Ubon Ratchathani in the Northeast and was founded by disciples of the late Ajahn Chah. Very much a forest monastery devoted to meditation.

Another forest monastery in the Ajahn Chah tradition is Wat Marp Jan near the Gulf coast in Rayong. I believe the abbot there, who speaks English, is open to long-term meditation students as well. https://watmarpjan.org/en/

There are many other monasteries that might work out for you. Best idea is to come here first on a tourist visa, pick a monastery and try a short stay. Then, if you want to stay longer, look into transferring to one of the visa options explained by Ubonjoe and ask the abbot if they can sign off for it. 

I compiled a list of meditation retreat options in this article from late last year. It's not exhaustive but includes most of those known for providing assistance in English. https://www.travelfish.org/beginners_detail/thailand/133

Is a few thousand at a campaign rally even significant when you consider that hundreds of thousands of people are cramming into sports arenas on any given night in America? If they cancel political rallies, how long until NBA games start being played in empty arenas, if at all? What about March Madness? And baseball season is right around the corner too. 

Pearl Jam just announced it's postponing an upcoming tour. How is a packed concert any different from a packed basketball game or a packed political rally? 

When sorting my yearly extensions I always do exactly what the IO checking my docs says while being polite as possible and never talking back or "pointing out" that she's wrong. It's usually the same woman (I use One Stop Centre) and she always tells me to make copies of docs that I've already submitted. I don't even say "I already have those copies." I just go pay the 2 baht for another copy and let her see her own mistake without letting on that I know she made it. I play dumb, because that is what she prefers. The process has always gone very smoothly, eight years now on the same visa.

On the other hand, I saw another farang applying for extension with the same IO checking his docs, and he was getting into it with her, saying "I already showed you that" and "the rules don't say I need that" while giving her attitude. Well, she proceeded to make it all take much longer than normal for him, finding some tiny sticking point to make him "correct." 

There are true matters of principle that are worth fighting over, and then there are people being jobsworths over minor issues like photocopies. Thai immigration is full of jobsworths -- best to humor them and play dumb because it's simply not worth the hassle of resisting, in my opinion. 

Not going to comment on budget and visa issues as others have covered that well.

BUT, on the subject of good locations for digital nomads, I'd personally opt for Krabi over Chiang Mai, and I'll share my experiences having priced out rooms there over the past year (still have a residence in Bangkok so have yet to make the move permanent, but Krabi is already like my second home).

In Krabi province there are several different places where you could live... To start, in Krabi town you can rent a basic room w/ no kitchen in a shophouse for as little as 2,000 baht per month not including utilities. Then there are the beaches. Many long-term rentals available near Ao Nang in the 6,000 to 10,000 baht range, for ex. near Ao Nammao or in Khlong Haeng near Haad Nopparat Thara. Place I usually stay in Khlong Haeng is a small apartment without kitchen, but with fridge etc. and plenty of space, for 8,000 baht a month.

Then, between Khlong Haeng and Khlong Muang (or in the latter itself), I've checked out large air-con bungalows that go for 6,000 baht per month. The one I nearly rented had a small kitchen space; all that would have been needed is a 1,000 baht hot plate for cooking. 

Ko Lanta has its own decent long-term options, although there you pay a bit more for an apartment and the internet tends to be slower. I prefer the mainland. 

And Krabi province is absolutely beautiful, with many good beaches and easy access to countless islands. The area is home to many expats with plenty of fun nightlife and a relaxing, easygoing vibe. I spent 7 years traveling Thailand on a professional basis, covering all parts of the country, and IMO, Krabi is where it's at for long-term life based on freelance desk work. (Although Ko Chang, Ko Phangan, Chumphon and Prachuap are all fine options that I've considered as well.) 

I've had a Non-Imm M visa and related work permit for six years. If you do most of your work for an accredited and legit media agency, ask if they'd consider sponsoring you.

They'd have to write a letter stating that you are doing work for them which requires you to be in Thailand, plus a second letter describing the nature of their agency. If the agency is somewhat obscure, as is my employer, the MFA will check in that country to make sure it's real and meets their guidelines. I.e. "Jim's travel blog" won't cut it, especially if Jim is both the sponsor and the applicant. But my experience proves that it does not have to be a major media company. 

You would then submit the two letters along with a bunch of other stuff via the online application here: http://mmos.mfa.go.th/   

As Thai govt online pages go, this one is relatively user-friendly. The various MFA people I've dealt with have always been polite and fair to me as well - it's a different world compared to Immigration. 

Without the sponsorship letters, you have no chance. Even with the letters, you will most likely be denied if it's obvious that you're a freelancer and not a full-time correspondent. So, ask your sponsoring agency to consider this when wording the letter. A copy of your contract with the agency is also required the first time you apply, as I recall. 

A month or so after submitting the application, the MFA will request additional documentation if needed (believe me, there is always something), or go ahead and invite you to the in-person interview that all M visa applicants must pass. I did this at the MFA in Bangkok because I was already in-country when first applying, but those applying outside of Thailand are interviewed at their nearest Thai embassy. 

As others have noted, it has become difficult for freelancers to acquire this visa type. Prior to a few years ago, legit freelance journos could acquire it by seeking sponsorship from any of the agencies they do regular work for. The junta changed that. 

If you are successful, you can't ask for a better long-term visa for Thailand. Once it's issued, work permit and press card come automatically. Well, you have to go apply and pay for them, but MFA will supply you with letters that trump the judgment (or mood) of any Immigration official. MFA has rank, in other words, and they're the ones who decide if you should be here, not Immigration. Yearly renewals are straightforward, but you have to get the same media agency to write a new letter every year and submit clips showing that you are still working for them. Best of luck if you go for it.