The regulation is "no less than 65,000 baht per month". So basically you should be fine if you get total 65K baht transferred internationally every month. But best is check how your local immigration office treats those.
Be sure you keep current banked funds following requirements until you get next extension approved.
, luckily, Chaengwattana accepts an extension application within the last 45 days of your current stamp. You should be able to manage your application in time, I guess.
That order is about the requirements of mandatory insurance for 1-year extension based on retirement for those who has entry stamp based on Non-OA. You don't have to do anything with police station for 1-year extension. You just meet the requirements including insurance to apply for an extension based on retirement.
It is a "police order" because the immigration bureau is a part of Royal Thai Police.
, Your current extension is until 9 October. You leave the kingdom 27 September. You don't have to ask for "earlier processing". Most offices accept 1-year extension within the last 30 days, that means you can apply for your next 1-year extension on or after 9 September. You should have enough time to apply for your extension before your travel as long as your employer provide the documents in time.
, AFAIK, Chiang Mai issues an extension on the spot, same day. If you already have a plan to travel out of Thailand, i think it would not be a bad idea to talk with the officer about your travel schedule when you go there in 28 June.
You will receive in-country Non-O and 90 days stay stamp on 28 June. Then you will go back to the same office to apply for a 1-year extension during the later half of this 90 days. Chiang Mai accepts your extension application when your stamp remains 45 days or less. Get the latest requirements list when you go there on 28 June.
You are at the first part of the whole process of in-country visa/extension applicaton.