You really need to read the requirements on the Thai visa website
You can enter on visa exempt for 60 days but if you want to retire in Thailand and are over 50
Apply for non O visa from home, ensure 800 K THB in Thai bank account for minimum 2 months and then apply for 12 month extension based on retirement at immigration office
I have no idea how you do it once in country but again if you read the website it will be outlined for you
ok but I have no idea how that meets Thai visa requirements as I’m not American. The 2 week holiday is up to you but doesn’t help nor hinder the visa process
Read the requirements, as a starting point, and ensure you meet all of them
Then get an non O visa at home, go to Thailand, open bank account, deposit required funds at least two months before your visa expires, go to immigration and get an extension based on retirement