IMHO if he moved to a cheaper rental in the very early days, and the owner did not report where he was staying, it would have been easy to get "lost" in the system, especially if he did not bother to report to Immigration in the first place. When he moved to Chiang Mai he probably did the same thing which obviously worked for him.
The 90 day report only works if you report to Immigration in the first place, and the TM30 only works if the hotel/guest house/building owner submits the TM30 form to Immigration as well.
I don't think that every place in Thailand does that.
If he was not married to a Thai, kept his nose clean and caused no problem, most Thais would accept/believe that he had a visa and mind their own business..
How did he renew his passport? I have no real idea, but he may have sent it to a friend or a relative in the UK to be renewed via the Post Office is one possibility.
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