I did not read any exception for AirBnB house owners:
The law: According to section 38 of the 1979 immigration act, "Land owners House owners, the possessor, heads of household, landlords or managers of hotels who accommodate foreign nationals on a temporary basis who stay in the kingdom legally, must notify the local immigration authorities within 24 hours from the time of arrival of the foreign national." If there is no immigration office in the province or locality of the respective house or hotel, the notification is made to the local police station.
The Visa Exempt Scheme gives you 30 days on entry, it can be extended once with another 30 days based on tourism at a local Immigration Office, NOT on the airport.
If you plan to stay longer than 60 days, get the Single Entry Tourist Visa before you make your way into Thailand and get 60 days on entry and this can also be extenden once with another 30 days based on tourism at a local Immigration Office.
The Single Entry Tourist visa can be extended once with a 30 day based on tourism.
After that it can be extended on several reasons but that means you must have the correct documentation to prove the reason.
As example: Visiting family, marriage certificate and id wife
Medical Extensions, letters from Hospitals and doctor
Do not plan that your friend is unable to travel, airports allow people to leave and land borders are open. If your friend wants to stay longer, pick another visa like the Multiple Entry Tourist Visa which can give him almost 270 days inside Thailand.
The seasoning requirement is for the 1 year Extension of Stay, First he need to get the Non Immigrant O visa.
15 days remaining in Bangkok, 21 in Chang Mai, it depends on office, but ASK Immigration as when he goes to apply for the 30 day Extension of Stay based on tourism. AND ask the list with requirements.
To apply for conversion to a Non Immigrant O visa based on marriage and later for the Extension of Stay based on marriage the person needs 400.000 Thb on a Thai bank account. You mention he has only 250.000 Thb, which means not enough so he has to travel to a Thai Embassy who hass less financial requirements like the one in Savannakhet Laos.
OR
open a new bank account on his own name and transfer 400.000 Thb for conversion to the Non Immigrant O visa and later the 1 year Extension of Stay at a local Immigration Office.
It sounds like a plan, but talk with your employer if he can apply at Immigration for conversion of your Visa Exempt Entry or the Extension into a Non Immigrant B visa.
If you arrive before 14 Oct 2022 (valid until date of the Non Immigrant O-A visa) and you have a valid insurance for 1 year you get a new 1 year of stay stamped in your passport.
BUT this stay is NOT a multiple entry stay as your visa is not valid anymore.
If you like to travel during that period, you need a single or multiple re-entry permit and get the same Admitted to stay date on return (as you think Sep 2023)