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If it were my project, I'd upgrade to the last 1.2 version first. It has
deprecation warnings for the upgrade to 2.0. Fix them, then upgrade to 2.0.
Check everything into version control. Then try upgrading to 2.3.11. Fix any
warnings and run it for a bit to shake the bugs out. Then upgrade to 3.0.6.
There is a plugin or gem, rails_upgrade, that checks for deprecated code.
Unfortunately, it is not being maintained. From discussions on the rails-core
mailing list, is sounds like someone has forked it and is maintaining it. It
will help. But the 2.3 => 3.0 upgrade is a many day process.
If Ryan Bates has a Railscast on the upgrade, watch it. His screencasts are
uniformly excellent.
HTH,
Jeffrey