many travel insurances that have some work & travel packages. you can even take your normal travel insurance that is valid for around 50 days per trip and extend it. just talk with your travel insurance company what options they have… you do not need an expat insurance that will cost you hundrets per month
In your case i would take a travel insurance from your home country. sign a policy for the length of your stay. that will be a lot cheaper than the thai or expat or nomad insurance packages that people try to sell you here. in germany for examply i use a work, learn & travel policy from Allianz which costs me 1,25€ per day with full coverage. can even do up to 2 years on one contract.
most stories i read are digital nomads / freelancer that use wise for their banking. customers / companies paying them on that account. and then they get locked out. happening all the time… its a pretty dumb idea to have large sums in a service that isnt a real bank. Wise is great for transfers, but not for holding money.