Chiang mai immigration accepts a extention from 45 days prior to expiration. You can do it anytime. Do it in Chiang Mai. And as Tod Daniels mentioned. Do it in Central Festival. 2th floor.
You can apply in Thailand for a Non O, 90 days single entry visa based on retirement (50 years of age).. Many have done that. before the 90 days expire you can apply for a one year extention of stay.
Having the correct extention date is important when stating the proces of getting a non O visa. Starting wrong means your extention date will be the wrong date forever. It can not be moved or altered in any way. Sometimes its better to start all over again with a good planning to make sure the extention date will be in a period you will most likely be in Thailand every year. Taken in to account that the 30 to 45 days period in advance to extend your stay gives you some limited flexability.