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This question was answered by @sierracircle:
I use this method:
http://blog.netgusto.com/solving-web-file-permissions-problem-once-and-for-all/
which allows me to have www mounted in my users home folder. Anything I add to that www folder as my user will automatically have permissions set for www-data
It works great, and takes only a few minutes to set up, and solves all those permission issues for www-data
The tutorial sets it up for a user called devone, but I just changed that to my username