Q. Is it possible to do this all online or do I need to visit an Immigration Office?
-> You have to go to the office in person. There is an eExtension service, and you can apply with an extra fee added to the official fee, even though, you have to go to the office in person to get a sticker on your passport on appointment date with eExtension service.
Q. which Immigration Office would you recommend?
-> It's more like depending on from where you go to the office.
Q. can I apply 2 weeks in advance?
-> Yes. The Chiang Mai office accepts extension applications within 45 days of the current stay expiry.
Q. can I make photocopies of passport and take passport photos at the Inmigration Offices?
, That's correct, you have to apply for an extension for the same reason as your entry/initial stamp. You can change the reason for a 1-year extension when you already on 1-year extension.
Yes, it's possible if you do carefully. As you say, you need documents from two branches for next application.
BUT,
better to talk with your local immigration office before you move money. Some offices don't prefer those steps. Some don't have issue for you to do that way.
Q. can I do a one month extension on a one year non O retirement visa ?
-> No, there is no 30 days extension on Non-immigrant based visa/extension. What you can do is applying for an extension by meeting all requirements for 1-year extension, and try to ask for shorter validity.
Q. how long before it expires
-> You can apply for an extension within the last 30 days of your current stamp at most immigration offices.
Q. do I have to do it at the same time or is it ok when I just go for the extension ?
-> That depends on your current stamp. Go to the office to apply for an extension and ask when is your next 90-day report.