I frequently have to travel with bags and parcels too big to carry on. I've had very good success with checked bags in situations like the one you describe. The baggage folks tend to do a pretty good job of moving baggage between AA and AE flights, especially at ORD and DFW, and even in the case of a tight connection.
Of course, I also tend to follow
beerup's rule.
Originally Posted by
beerup
Why not carry on all your essentials and check the illegal-to-carry-on items? If they don't make the connection then you should get them 24hrs late (delivered to your destination), but surely that's better than not having them at all.
I pretty much always carry on enough to last me a night or two, in case the checked luggage doesn't made it.