Take more UPTO
Microsoft announced that they are doing away with their traditional PTO system and giving everyone "unlimited" PTO.
So my advice to you is to get a job at Microsoft. The 1099 life is for suckers, since we generally only get UPTO - Unpaid TIme Off.
What I do advise though, is to take more UPTO as a 1099.
I generally sprinkle in half days, Friday's off, and a couple of multi-week vacations.
The obvious trade off is that you're leaving a few bucks on the table, but I've found the psychological benefit of going on lunch date with my wife on a Wednesday or building in a few post-vacation days off to rest and get over jet lag to be worth it.
When you go 1099, what will you do on your days off? I'd love to know.