UNIX for Advanced & Expert Users

Hi:

(I apologise in advance for the lengthy prelude--but i think it's necessary to properly ask my question.) I code in Ruby and Python on Mac OS X. Ruby, for instance, as i suspect everyone here knows, is both open source and it it lacks native support for e.g., GUI and Image Manip. These two characteristics are the root of the problem (actually my lack of knowledge is the problem). For instance, in order to successfully package even a simple script in Ruby, I nearly always need Tk/Tcl (+ Ruby Bindings), ImageMagick, and several Ruby Gems (Ruby's package mgmt system, like Perl's CPAN). Because these are separate from the interpreter, they are installed separately, usually from source (though there are nearly always binaries available). So often, when i an upgrade to any of one of these core pieces comes along (or a reference upgrade to OS X, or even sometimes to my editor) it takes me forever to get things working again. No problem with the download/compile/config/make/install--that's more or less trivial. The difficulties are after that--e.g., i know i have both ImageMagick/RMagick installed on my box, that they are in their "proper" place, and i've got all dependencies resolved--but i just can't get them to find each other when it comes time to execute the script. I always get it fixed--but in a very ad hoc, duct-tape sort of way, that i read on a Ruby forum, etc. and that i don't really understand, but it just works. I hate that. What i would really like to learn in a systematic way--but i can't find the right sources--are things like: how to diagnose these problems (by deciphering the bash error msg? unit test, etc.?), and then how to solve them (e.g., by adding header files? by symlinking files to another directory, etc.?). Again, i'm not after a solution to a particular problem, rather i'd be grateful if someone could point me to some sources that i could study and slowly develop some sort of map to troubleshoot these sort of problems in a systematic way. Thanks for your consideration and for reading this way-too-long Q. cheers