The way I solved this back when I was using the rails app was:

- I put all my library files into a common dir

- I added a line of code to each test script that allows it to find and add the 
lib dir to $LOAD_PATH

For this I use the same idiom from some of the Watir unit test files (in this 
case it will add the dir one up from the top-level script to $LOAD_PATH):

$LOAD_PATH.unshift File.join(File.dirname(__FILE__), '..') if $0 == __FILE__

So, you might be able to do something like this:

1. In the runner/data dir, create a new dir called 'lib' and copy your library 
files to it

2. In your test scripts, add the above line of code at the top

3. Then change your require statements to reflect the lib dir:

require 'lib/library_file.rb'

Aside from testing this using the runner app, you can test the changes manually 
by cd'ing in a command window to c:\ or some other random dir, then try running 
your script from there (ruby c:\foo\runner\data\suites\test.rb).
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