The best set of instructions I have found for setting up the open source GIS tools I know and love on my Mac is here: Installing Open Source Geo Software: Mac Edition These instructions are pretty complete and worked well for me on Mavericks.
I found I had to install pillow to satisfy the requirement in tilestache for PIL.
sudo pip install pillow
It took several hours to install Mapnik; skip that step if you don’t plan to use it.
In the past I used stackbuilder to install postgresql and postgis on my Mac. I removed that version and install with brew; what could be easier than
brew install postgresql
brew install postgis
I had to hack around a bit to get postgres set up. I created /usr/local/var/postgres/9.2/main by adding “export PGDATA=/usr/local/var/postgres/9.2/main” to my .bashrc and then running initdb. I had to do the command “createdb” to get my user created so that “psql -h localhost” would let me connect to the server.