If you arrive on the 1. December and fly out on the 1. January at 2am, you will go through immigration on the 31st December, so absolute no problem. At worst, you'll pay 500THB.
Only if you made the first 90 day reporting at an Immigration Office.
After that it's very easy to do on-line and only takes a couple of minutes. Then it takes between a few hours and several days to get the approval notification.
Sorry, my bad. Well in this case, you can apply for one 30 days extension of stay.
In an emergency, you could always apply for a second extension. Then you'll get a stamp saying "Extension Denied" and an order to leave the country within 7 days. You will also need to sign a form where you acknowledge that you understand the implications of overstaying those 7 days.