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Break it into two tables on the report, first is Kitty Servers and their installed Software and second is just Kitty Servers with Windows Updates. The Software inventory and Windows update information are stored in separate database tables, and if you know SQL then you may be able to see why allowing the users to just join together any random tables they attempt may give unexpected results. So the devs built some limitations in to the web tool limiting the number of ways you can connect things to only the kind of simple joins they planned for. Looks like they didnt set plan for Software Inventory and Windows updates to be side by side.
If you don't like that then you have to get into basically writing the report using fully custom SQL/SWQL that would be able to do a left join from the nodes table to the software inventory and another left join from nodes to the windows updates.
Thanks for the response. I wasn't sure how I overlooked the "Add Content" option right in front of me. I'm still new to the system and learning it. Once I was able to add content and bring in a new table everything worked as planned.