Is it a safe city?
Can you walk in random directions without fear?
How difficult is to get visa?
Do they speak English?
What kind of expenses are you looking at monthly?
As someone with fully remote job, I am wondering whether I should go couple of months there. I am on the verge about it.
Random walking is my all time favourite thing to do in Bangkok. Although I'd recommend getting out of the CBD. Yes, tech events are great, but I prefer the slower, quiet pace of somewhere like Southern Phuket, or the diving in Koh Tao.
Visa is trivial, English is everywhere, if you're splurging, you could spend however much you want, but it's easy to live cheaply. Rent is something like USD500-800 for the month if you don't even shop around. Food is pretty cheap that I'm not even sure how much stuff costs. A 1 hour massage is about USD10, although you could splurge to about USD20 if you really want to.
That said, while I love Thailand, I'd have to say that Vietnam is still my all-time favourite SEA country to visit... but Thailand does keep drawing me back. I have a favourite beach spot and Kana Moo Grob really hits the spot.
English is spoken almost everywhere, at least basics. 35m+ people travel to Bangkok every year and the tourist industry here is large.
I spend about $800/mo on rent but I have a very nice condo with gym + pool within 5 minutes walking to the sky train close to the center of downtown. I also do month to month with no contract, if you do a 6 month contract you can find a studio for $200/mo ~15 mins walking to the train - I just prefer convenience and luckily make enough income to cover the costs. Maybe spend another $500-700 a month on food and transportation.
Going out to eat is about the same cost and buying food/cooking and the food delivery services here are great (either free delivery or 50 cents for delivery). Most my meals average $5 usd but I usually eat at higher end place, you can do $1-2/meal if you want but it's lower quality food and ingredients typically. I like to go out, but don't drink often so alcohol isn't a big cost in my budget. Beer is usually $3-5 a bottle at most bars compared to somewhere like Vietnam where everywhere has beer for $1.
I initially went for 1 month (1 week in BKK -> 1 week in chiang mai -> 1 week in Koh Lanta -> back to BKK) and ended up staying for 5 months total the first year while traveling to Cambodia and Vietnam for visa runs. I definitely recommend 3-4 weeks your first time to see if it's for you with a similar route to me to get a feel of the different cities. I liked chiang mai more at first but grew to love Bangkok the most now.
Don't worry about booking much accommodation far in advance as there's much readily available. I just like to book a nice place for my first week to recover from jetlag before I head out and play the rest by ear.
Hope that helps!