I haven't tried running buildr on OSX, but did you try using buildr with jruby instead of ruby? Buildr with CRuby has to rely on a C library rjb, which I wouldn't trust to work as well as jruby and from what I've seen only reliably works with Java 1.5. The latest JRuby just added nailgun support too, which, though I haven't tried it, is supposed to reduce the start time of JRuby significantly enough to make it viable for rapid command line use.
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