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Let me check for you the different types of long term visas available here and conditions. Obviously mine is work permit that requires to be renewed annually and had been doing this for the past 4 years. (they rarely give more than a year as what I heard cos the agencies that help foreigners get visa legally charges quite a bit and pay coffee money to immigration so this is a constant income for them but its worth and fair).
I do not think he has much options. Visa run is the only cheap option for him.
Drift does not seems to want to set up a company in Thailand. He can do his own visa run up to 90 days and then using agent help to get another 90 days. So this will set him and his wife up for 6 months. Do that every 6 months. That is tourist visa. But pls check the law for that if the thai authorities will ask you for coffee for this. My farang frens uses a mixture of all these to stay long term.
Or Both of them can sign up to learn Thai language but that is only up to maxi of 5 years with yearly renewal and they will test ur thai language skills yearly. So this is not a very good option for him if he wants to retire.
Or he can use a fake company. hehe.. check with property agent. Many farang do that to own a house but got to pay the property agent all the fees for that. I do not recommend this unless you have business or welfare system in other country to feed you.
My personal choice is to find a job in thailand or have a real business in thailand. and then marry in thailand. That means to middle finger the sinkie govt while enjoying life elsewhere without much legal hassle.