With your history you took a big risk flying into BKK without fast track. That system-level note sounds cursed. Most immigration offices are now likely to deny future tourist extensions, so you'd be doing a border run (or fast track flight) every 60 days. Get a DTV.
My friend with experience in this situation said your son is a special VIP visitor who should book airport fast track service through a reputable visa agent. Cost: 2500-4000 THB.
Faster and cheaper than 'get a proper visa from Malaysia', or doing a land border entry. He also said that whoever bothers with a sob story with a 'return flight', 'proof of accommodation' and '20k THB in cash' is simply not appreciating the game.
Consider reapplying on basis of soft power (a few dentist appointments) and keep Thailand out of your professional situation. That will save you a lot of nosiness and headache.
Getting DTV with a single medical appointment seems preferable to voluntarily giving Thailand insight into your employment/business/income history, complete with a cucked letter saying the slave is 'allowed to work from remote'. Thanks for your Jakarta report and enjoy your 5 year visa!
I went together with a friend and his visa expires a few days before mine. He received a "under consideration, return next week" date, but right below he already got the full extension, dated until the end of August.
Unclear what we will get on June 24, or whether my friend has to return at all.