If you have a multiple re-entry visa and always get stamped in for 90 days? You can enter Thailand on 1st June and get stamped 90 days. Then get a re-entry permit for that stamp before you leave.
It could well be possible to register to online reporting with just the rental contract. Why don't you try? There is the option "pukropkrong" instead of jaobaan there. It means the occupant. And a fourth option olso, others, not sure for what. So I would definitely try. I would send the tabienbaan and land lord's ID as well if available. Actually the rental contract must include at least the ID to be legally binding. And it must include the tabien baan number and correct address, so yes, better you get the copy of the first page tabien baan and jaobaan data, if it's same with land lord's name in the rental contract and the ID. Can't fail with that. Get the copies signed as well and scan.
Hotels must do tm30 registeration by the law. You mustn't worry about that. If you stay with a friend or in rental, you should make sure to get it done. Many landlords are aware can take care of it online in CM. But better you ask a print out. Hotels, no worries.
As already mentioned, you can leave Thailand as often as you want on the O-A visa and it will always stamp you in for 365 days within it's validity data, which is one year. So you will still get stamped in for 365 days if you were to enter Thailand on it's last valid day, giving you effectively another year. After the visa has expired and you stilll have that 365 day stamp you must buy a re-entry permit if you want to exit Thailand again and not loose that right to stay. So be sure to get the re-entry permit for that "second" year.
Ok, Thanks. Then he must hold on to the 400k that extra one month. I figured they could give him a break and just give him the 365 days next if done this way but guess not.