Why dun you save all the issues And return to Thai when the boy is 16 plus 1 day. In my recollection from immigration, he is considered an adult and liable to overstay fines, hence, any challenges will be at the consent of your son. Just my thoughts for your considerations
Your return air ticket will be scrutinised by your flight airline on boarding. Immigrating seldom check flight return ticket unless you are determined to have utilised tourist visa to stay in Thailand for too many times in a year and depending on office u visit.
Landlords are obligated to file on first take up of the residence, hand you the tm30, it is tenants' own duty to ensure updates on their own movements.
Bring her passport, medical certifications, tm47 filled, last 90 day report, go as a parent to the 90 days reporting counter. Copy of birth certificate in case justification is required. Better if you had the copy utilised for application for extension of stay for the birth certification.
have a marriage than let your Thai wife introduce you. Depending on immigration office they will not issue visa on the marriage date itself, generally marriage visa stands test of time, unless at time of marriage, your wife is verified pregnant. Do the visa yourself, not that difficult admin work the wife in future's assistance
My own experience, they tend to follow the rules as officers' files at immigration are audited by federal. It be foolish for any officer to sacrifice their career prospects for something obviously detectable by the auditors.
What are you needing to cone to terms with, every humans these days exploit in some way unless you seclude into caves and jungles. There is always that hope of fulfilling their ego centric self, exception, the ones that already reach high maturity and accept what their lives is to be, in which case, they attained and resolve into modesty and humbleness. You will need to find this lot of individuals. You just need to select whom you wish to transact with.