Answers do not change.You did NOT apply for the Non Immigrant O visa based on being over 50 years of age, but you applied for an Extesnion of temporary stay in the Kingdom and got a big stamp with a new 1 year period.
And then this: "His HR tells him if he doesn't apply for a visa in PP he can't apply for a work permit. "
Altough work permit application is not part of this group. the employer is now using the application method 3 because the foreigner does not have a legal stay inside Thailand to apply for the Work Permit, but after he changed into the Extension of Stay based on marriage the employer can apply using application method 1.
I deleted a few comments. Sorry but Thailand has long term options to stay legal in Thailand according your purpose of Stay. As mentioned earlier for those who do not have to work there is the Thai Elite Visa, for those who work and it does not matter what name you give yourself, the Non Immigrant B visa.
People get denied entry, it is part of the job of Immigration at an Airport., it happens world wide, but USA, Canada, Australia and UK even made a serie about it to be watched on youtube.
Be careful and if you hear that your friends is denied, try to get some information before you post, it saves a lot of discussion from people assuming what happened. Thanks.
Okay, you can apply for a new Extension of Stay based on what ever reason, if you do not meet the requirements, your application will be NOT approved and get 7 days to pack your bags and leave the country.
That is not a tourist extension, but it will give you some time.
You can not apply for or get a Tourist visa inside Thailand. I have no idea what you mean with a working visa as such thing does not exist in Thailand.
You must have a Working Permit from the Ministry of Labor and a Visa or Extension of Stay that allows working in combination with that working permit. Two different things.