Didn’t read the bit about before entering Cambodia, just read it as on return.
The TM30 bit is dependent on the immigration office. Some insist if you stay in a hotel and return home, some only if you go overseas and return home and some don’t care if you’re returning to your home whether you’ve stayed in a hotel or returned from abroad.
You can get a re-entry permit at anytime prior to leaving. If that’s day one or on the day you fly doesn’t matter. If you do it at an immigration office they’ll probably want to see that you’ve had a TM30 filed. If at an airport they won’t care.
You don’t have to report to immigration. Your house owner reports you as staying at their property (TM30). If it’s a hotel they’ll usually do it by default. If a private house then that house owner can either report in person to your local office or just do it online which takes a couple of minutes.
The process is easy. Depending on the office you use will determine how fast it happens. In Bangkok probably a few hours. My guess in UT would probably be 15 minutes or so.
Your 90 day visa is a single entry visa. Once you enter Thailand you no longer have a visa. It’s used. Finished.
What you have is an entry stamp allowing you to stay for 89 further days (entry day is day 1).
If you want to leave and keep that entry stamp “alive” you’d need a re-entry permit. On return you’d be stamped in for the exact date you were originally given.
Each entry needs a TDAC. Each time you return your house owner (or hotel) should in theory file a TM30.
Yes on each new entry you’d be given a new 60 day exemption stamp.
That said you can’t live in Thailand by constantly border bouncing, but what you are doing is a typical tourist type thing so should have no issues whatsoever.