My advice is to spend a week paying off any testing arrears that you have accumulated, and then do the update in one fell swoop.
Where I work, we updated a very large application from 1.2 to 2.0.2 last summer and at the same time updated to Ruby 1.8.6.
MUCH MORE was more than expected. The application used several old functions that were removed or deprecated (for example, ActionWebService), so it took some time to convert them. But basically, we came up with a lot of subtle bugs, such as small differences in how the switch options work, some of which were related to the Ruby update (versus Rails).
In some parts of the application there was a spotty coating. If we went into it with the best tests, everything would be much simpler.
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