@Junior *****
I think you might be confusing getting a new yearly extension with applying for the initial 90 day Non-Immigrant Type visa from a free entry stamp or tourist visa entry.
That process does indeed require you have so many days left on your existing stamp before you apply for the visa because of the 2 to 3 week "under review" period.
BUT
yearly extensions of stays (no matter if it's the first year or subsequent ones) can be applied for right up to the day your current stamp runs out