Perhaps apply directly for citizenship is easier. You need to work, pay taxes, make all the residence duration anyway. Give it 5 years to prepare to apply, meanwhile learn Thai. Give 5000 baht to Charity every year and get receipts. I support the Girl Guides of Thailand.
Depends on your local office. I own my condo in Chiang Mai. Last year I had to pay the 1600. Now I go everytime I come back to Thailand( almost every month). It is reported CM Gives 7 days leeway for “update same address”
There are a lot of police checks these days. There is a remote chance of being busted and jailed in IDC before you get to the airport. An overstay remains on your permanent record. If you get a stamp in your passport other countries you may visit (example Japan) or apply for a visa to might not like that. Overstaying is never a good idea.
Never overstay. Some other countries don't like overstay stamps. (example Japan). A Long shot but You might get busted and jailed in case of random police check.