Lived in Bohol. (Tagbi area) and Phuket (Rawai). In one place I was hit by other bikes and could never leave my helmet when parked. I made the country where I did not get hit or worry about helmet my main base. And visit the other.
my understanding is everytime you enter Thailand from another country you get a stamp. It is from that stamp you have 364 days to report (you lose a day so it's not 365). But at the 5 year mark no matter what you have to do apply again for the second 5. So essentially with the LTR if you leave the country less than a year each time you know report at 5 years. TM30 still applies.