Interesting use case. My intention with checkconn though was for first time users dealing with corporate firewall / proxy servers. The goal being to point them in the right direction of troubleshooting their network and security software, not GAM 🙂
The feature is still in development and not in any release version yet. Currently it will always exit zero but can see about non zero exit code should any failures occur.
You certainly could run it before scheduled jobs, though I'm not certain how necessary that is.
Ross' version is what supports JSON output so it's for him to decide that.
Is your Internet connection that unstable?
Jay