@Brian *******
you're totally able to apply for your yearly extension from 30 days before your stamp expires right on down to the last day of your current 90 day Non-O entry stamp.
BUT
Cutting it to the last day or so means IF you don't get it right, you're gonna run on overstay to sort it out ๐ฎ
and
It's totally up to the immigration office as far as if they would let you run on overstay and then apply for the year extension while you get the documents sorted or you exit/re-enter and start the whole process from square one again getting a new Non-O visa
you got here this week, if you get the funds in within 2 weeks you'll have at least a week or so left on your current 90 day stamp when you hit the 2 month seasoning of funds mark. I'd go to the immigration office after you get the funds here, get the hand out listing the documents required and be ready to move on it as soon as you can so you have time in case you don't get it right the first try ๐