In the first scenario where you are using AP rules, have you tried simplifying your rule? i.e. when defining what to block just start with one file type.
The rule parser might be having issues with the multiple statements. If it does work, you might need to create multiple rules.
In the case of user-defined items, we'd need to see what your OAS policy is because you might be inadvertantly excluding these files from scanning.
But also, you should clarify which file(s) you use to test with to check if it's working.
There are quite a few needs here so it would be best you work with a Support technician and open a service request.