Age 57 retired US citizen.

Part 1.

I arrived in Chiangmai on a visa exempt 45 day stamp and extended to a total of 74 days. I just went to Hanoi for 30 days and I arrived back in Bangkok on a visa exempt and will stay the thirty. I plan on leaving at the end of the month for at least 90 days to Malaysia, Vietnam and Cambodia. So that will bring me to October will I probably be able to stamp in again in October?

Part 2.

I am retired and do have documents that state me pension is $65000 annually from the NYS pension system. I will not be returning to America for quite some time. How difficult would obtaining a retirement visa be based upon income.

Where would I start. I don’t mind moving around for the current year but I would like to try to stay in Thailand longer periods by next spring.