Is it possible to connect OCS inventory to JIRA ?
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.
Are you still thinking on that? the asset management is a big gap on Jira
Insight has massively improved in the last half-decade, to the point where it's better than OCS
But, Insight has an agent? Could I Get the System info from the Windows computer in an automatic way?
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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