Success story (finally). First of all, thank you to the members of this group who had the patience to respond to my questions. This is a great community. I'll try to pay it forward and help other members as well.
It got approved in a little over 30 *working* days since application. It was high season and both my embassy and the Thai one had some holidays. You can consult this on your embassy's website. Still, after seeing so many people getting their visas in just a few days it was pretty discouraging. Makes me think some countries / passports have higher priority than others. But now it's here so here's how I applied and the docs I provided:
Applied for "Workcation (Digital Nomad / Remote Workers)". I had two previous entries in Thailand one on VOA and one on tourism visa.
It's great that you don't need to have flight tickets purchased, you can just fill in your expected flight no.
For accommodation - I booked a hotel for 1 month after my expected arrival. I made sure it had free cancellation up until 2-3 days before my expected arrival in case I wouldn't get the visa in time. But other than that I had no long term rent or anything.
Proof of current location - photo of my ID card (not even both sides, just the front). This one is always strange, but it worked for me with my previous visa as well.
The docs - I could not upload the full contract with my employer because of upload size limitations. So I uploaded just the first page with the title and the signing parties and the last page with the signatures. I also uploaded the registration certificate of my freelancing business. Combined all these pages into a single pdf. The contract actually doesn’t explicitly mention that I work remotely. I guess it’s implied since my client is in a different country.
Because it was taking rather long, I sent them an email yesterday asking to estimate how much longer it would take and if I can leave the country while I'm waiting. They never replied but today I got approved WITHOUT any further request for documents. I don't know if me emailing them was related to this or not.
So let me know if you have other questions.
As a small side note - I happened to stumble upon the google reviews of my embassy and it had a ton of 1-star reviews from people that were upset that their visas were not getting processed in time for their arrival. Maybe some of them didn't consult the timelines (they are longer for the high season), but I'm sure a lot of them did. Anyway, if you see something similar for your embassy, maybe consider going to a country where you can apply in person and maybe you'll get your visa faster, if you have the means and if time is an issue. Just a thought.