Is it less stressful to file a 90 Day Report or leave Thailand on an O-Visa before the 90 days are up?

If you are not married to a thai, and you're gonna be over 50, you have two choices visa/extension wise

-get a single entry Non-O then apply for a yearly extension of stay inside the country by meeting the financial requirements of 800K baht banked in an account in your name the requisite time or a letter from your consulate stating you get 65K baht per month in income

OR

-apply for a year-long, multi-entry Non-O-A <- (note the A ;) ) at a thai consulate in your country BEFORE you come here. That visa requires a police back ground check, a medical certificate and proof of the equivalent of 800K baht in a bank in your country. It is good for unlimited entries for the year it's valid for, and each entry gets you stamped in for a WHOLE new year.

Seeing as there is no O visa that lets you stay here longer than 90 days, I'll take it you want to compare a yearly extension of stay (where you do 90 day reports at the immigration office) with a year-long multi-entry Non-O where you border-bounce every 90 days.