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Retirement Visa Question(s)

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Here is the information;

My friend is from the UK, 61 years old, here on a Non-Immigrant Type 'O' Multi-entry Visa issued from Hull. It expires on April 7th.

I know he can visa run before it expires & get another 90 days in the glorious "Land 'O Thais".

He just recently transferred the 800,000 Baht into the country, however it won't have been here for the 3 months prior to his Non-'O' visa expiring, which unless I am mistaken, is a prerequisite to getting the Non-'O' changed to a Non-'OA' long stay visa.

Now the question;

Can he go to a neighboring country (Singapore, Cambodia, Lao, Malaysia) once his money has been in an account for 3 months, and get a single entry Non-'O' based on retirement, then take that new visa to Suan Plu & have them extend it for a year, as well as buy a multi-entry stamp from them?

While this was a problem of his own making due to procrastination during this last year about bringing the money into the country. I am trying to find a work around which doesn't involve him going back to the UK to get another Non-'O' from Hull.

Any information would be appreciated.

All he needs is 3 weeks remaining on his 90 day stay (the entry visa may have expired) so he can make an exit/entry before the April expiration of visa and when down to between 4 and 3 weeks remaining do his retirement extension of stay. That will be in June so his money will have been in account for the required 3 months.

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