-If we work on WO5.4/Leopard and deploy on WO5.3/Tiger, what issue should we get ready to handle?
You should get ready to handle not doing this :)

Let's ask the other way around. How's our luck developing on WO5.3/ Tiger and deploying WO5.4/Leopard.

I seem to remember from WWDC that WO5.4 is intended to be downward compatible.
While I maintain that this is a really bad idea, most of the important things should work fine (the core API's are basically the same). It's not like API was radically rewritten, but definitely SOME API did. So you should be prepared that depending on which particular API's you call, you might find issues. It actually would be sort of interesting to see a javadoc diff (there used to be a tool somewhere that would produce javadoc diffs) between 5.3 and 5.4. I know of a handful of API changes that we ran into when working on Wonder, but I'm sure there are others.

Like Daryl said, plan to get comfortable with fixing XML component well-formedness issues -- I think that will be the #1 thing people run into.

ms

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