@Justin *********
hang about, you are confusing some things I said. To get a NEW in country Non-O VISA you need to apply when you have enough days left on your current stamp <- that was in answer to your bad idea of canceling this extension and starting over from scratch.
To apply for a yearly extension of stay you can do it ANYTIME you have 30 days or less left on your current stamp and you meet the requirements (as in the funds need to be seasoned the full amount on the date you apply not the date your extension runs out).
Same goes for the 60 day visit thai family extension, you can apply for that when you have 30 days or less left on your current stamp