First, Scruffy looks great! 

Second, I've had pretty good success installing ImageMagick and RMagick on both Mac and Linux (Fedora and Ubuntu) systems.  I did not use the port mentioned to install it on Mac, but did install all the dependencies with ports - basically, everything except RMagick, which I then installed as a gem.  The one painful part of ports, is if you are behind a firewall that prevents rsync.  Ports doesn't work in that case.  So, you either have to set up an SSH tunnel, or you need to do something like use a laptop outside that firewall to install the ports, then take the cached port files and copy them over and locally install.

On Linux, it was basically just a matter of using yum (Fedora) and apt-get (Ubuntu) to ensure ImageMagick was there (which installs any necessary libraries), and then again, installing the RMagick gem.  I will likely be doing this on Solaris soon, so can report on that once I try it.

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