The SCUD didn't work after I did all of that, but when I added a route for it, the SCUD randomly started doing its thing after 2 minutes and firing at 8:08:45.
(The main requirement for SCUD is that the engine needs to be turned on I believe, and you can do that by setting a route.)
For the Silkworm, everything worked perfectly with AWACS and the Silkworm SR after I moved it a bit closer.
Big thanks for everyone's help with the AI.