In order to make sure you have plenty of time to brainstorm, write, and edit your essay (or essays), I recommend starting at least two months before your first deadline.
The last thing you want is to end up with a low-quality essay you aren't proud of because you ran out of time and had to submit something unfinished.
Otherwise, start with the essay for your top choice school.
I would also recommend starting with a longer personal statement before moving on to shorter supplementary essays, since the 500-700 word essays tend to take quite a bit longer than 100-250 word short responses.
This week is known as Paideia after the Greek term signifying "education"—the complete education of mind, body and spirit.
What would you teach that would contribute to the Reed community?
That way you'll be able to see exactly what you need to do and when you need to do it by.
If you have one essay that's due earlier than the others, start there.
Doing so can save you some time and let you focus on a few really great essays rather than a lot of mediocre ones.
However, don't reuse essays for dissimilar or very school-specific prompts, especially "why us" essays.