I did it last year and I did it again this year. While it certainly took a LOT of time overall, I agree with the other posters in this thread -- the more you do, the tighter your stories get, and the better your applications get. People have posted time and time again not to do your dream school first. Why is that? Because the more you're exposed to the application process, the more you've taken the time to tell your story and to find the best examples for certain essays.
For me, by the time I got to my last R1 application, my essays were completely different (and better!) than the ones I wrote for my first R1 application. The stories were told more concisely, with more conviction, with more color. And ultimately, I went back and redid the first few apps I did.
While the idea of applying to a lot of schools is painful, and definitely hurts your wallet, your writing does improve over time. If you take the time to plan out everything -- how many essays you have to write, what topics are covered, when all the application and deposit deadlines are -- you can come away with a finished product you feel good about ... regardless of how many schools you apply to.
DISCLAIMER: I have not yet been accepted anywhere this cycle. My opinion, while optimistic now, could very well change in a few months time if/when the dings start rolling in