Your description sounds almost entirely like the existing call screening, so I'm pretty sure you'll be able to accomplish it. Start with call screening, and modify that to suit your needs.
It is indeed. This is already implemented in Asterisk I take it then? If so, brilliant news!

I'd encourage you not to give callers much information. If you tell callers that their number is blacklisted, or that the recipient is not available (and not offer them voicemail), they're likely to call back and provide different or no information. It'll be more effective to let them leave voicemail and then delete and ignore it. Just a suggestion.
A good one, thanks for that - will take it on board.

IP routing alone isn't actually sufficient (typically) to use multiple interfaces. Under Linux, you have to set up multiple routing tables, track connections, mangle reply packets (mark), and use 'ip rule' to select the proper routing table for the packet. If you haven't verified that replies go out the right interface, you should look. If you have, then ignore me. :)
This is already done and works, though from my (admittedly limited) understanding of the sip protocol I know that internal IP address information is included in the actual packet. I know that I could use sip helpers (kernel modules), but just wanted to know whether I should rely on Asterisk to do this or whether I should do it via netfilter alone (in which case why are all the nat-related options present in Asterisk?).

No... binding to 0.0.0.0 isn't a security risk. Typically applications bind to a specific address so that a single host can have multiple addresses, and an application or multiple applications can bind to specific addresses to implement virtual hosting.
I disagree. Binding to 0.0.0.0 allows connections to be made from all interfaces (provided the routing allows it, of course) - see my previous post as I do not wish to repeat myself here. I do not wish to solely rely on iptables/netfilter/other means if I can constrain Asterisk to the interfaces it is supposed to be using.

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