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This question was answered by @sierracircle:
I have had a lot of success using this method:
http://blog.netgusto.com/solving-web-file-permissions-problem-once-and-for-all/
I use the method he describes to mount the /var/www folder in my user home folder as www. That way I have access to it, and anything I create gets the proper permissions for www-data, while still giving my user access.
Took me all of 5 minutes to set up, and has been working for me for the last few weeks with no problem.