The problem is that this rapidly becomes unworkable for all but the smallest of networks with a huge amount of available time. False positives make this contest incredibly asymmetrical – ever think about how many hours went into developing IDS rulesets looking for malware signatures which were obsolete once people switched from IRC to HTTP? That repeated for HTTP to HTTPS, detecting “unusual” networks rapidly became ineffective as throwaway accounts or compromised hosts became popular, etc.
That process will repeat for every single bit of context you add. The worst case scenario for this is full-on steganography – public blogs posting scraped content with commands hidden in images or text statistics, bots searching twitter or subscribing to RSS feeds, etc. and waiting for user-triggered network activity before transmitting so it looks like just one more request in the 100+ made by a modern webpage.
For anything other than preventing DDoS attacks this is a slow, futile grind. It's much more effective to focus on preventing an attacker from running code inside your network than trying to clean up the mess after they do so. That's a combination of things like changing the UI to avoid asking the user to make critical security decisions they can't meaningfully answer and, most likely, an app-store like model for most people because even that level of review greatly exceeds what a non-expert can do.