I don't know about engines (I started w/ Rails after they fell out of style), but the general advice I recall reading is that you should upgrade a little at a time. For example, say you're on 1.2.3. You'd upgrade to to 1.2.6. Once you're running well there, you could go to the latest 2.0.x release, 2.0.5. Then repeat the process to go to 2.1.2 and then to 2.2.2 or as far as you want to go.
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