Also, I'm wondering what effect upgrading to Ruby 1.9 would have on legacy code from version 1.86. Is the new version backwards compatible?
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Some things are backwards compatible, but many aren't.
For a near complete overview of all the changes (including examples) in 1.9.x, check out Eigenclass's blog last archive.org snapshot of Eigenclass's blog.
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Sam Ruby has a good slideshow of the major changes: Ruby 1.9: What to Expect
Just to highlight a few things that could break your code:
- Single character strings
- {"a", "b"} no longer makes a hash
- Block variables now shadow local variables

Lolindrath
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