You are allowed open jaws and one stopover.
The first example is technically a circle trip, and I don't believe AA offers circle trips. Alaska does offer circle trips, but they may require that at least one of the segments be an Alaska flight. Maybe if you find an AA flight that also has an Alaska codeshare, it might work.

The second example is probably a valid round trip, since ORD,DFW,MIA are all valid connecting points MKE-SXM. The only problem is the 2 stopovers which are technically not allowed, but you could ask nicely, and if you're PLT or EXP they may allow it. Of course you could always book the MIA-ORD-MKE flights as connections, and then change them or fly standby after you "miss" them.