Hi Camilo,
1. Have you tried placing your images in ~/Sites/ as well?
2. The errors could be due to hidden files in chunk_includes. On Mac, Finder automatically generates .DS_Store in some folders, which usually causes Ibex to crash. I usually solve the problem in the Terminal, I move to the chunk_includes folder and I type rm .DS_Store.
This is an archive of the experiment I successfully ran on my Mac, if you want to try it yourself (and/or copy the server.py file in case you have doubts on the edits I describe in my previous message):
https://www.dropbox.com/s/x62tvt20e775i8m/ibex-local.zip?dl=0
