Yes, JIRA can hold links out to OCS items.
In the other directtion, as long as OCS can be made to issue REST calls to JIRA, then you should get links that way too.
I'd be thinking of writing a Connect add-on to link the two, I can't find such an add-on in the marketplace. But you need to define what you want from the connection before you do much more.
Insight has a scanning function that can run over your network and look for servers and services, but it's not an "agent" you have to install on every server you want to monitor.
Apart from that scan, no, there's no way to get system info from other computers.
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