It should be easier than this. I thought I had a decent Rails installation running on my MacBook Pro but TextMate was giving me some grief when shelling out to execute certain commands (like pulling down the schema for a model).
This worried me - my environment seemed OK, but if TextMate was failing then there's likely some other lurking problem. It took me about 2 hours to unwind everything and get my environment working so that I could see this.
The root cause? I'm not 100% sure, but here are a few hypothesis:
I think the concept of MacPorts is good, but in reality it shouldn't be this hard. My experience with apt-get on Ubuntu was about 100% better.
Oh well, all is good now. I absolutely love the new TextMate Rails 2 bundle.
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Disclaimer The opinions expressed herein are my own personal opinions and do not represent my employer's view in anyway.