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Creating an advanced search for specific checklist selections, by status?

I am attempting to create a checklist template and in return hoping to create a filter that can query the specific task and its status.

For example, box #1 "Icons Installed" & box #2 "Send Documentation" (same checklist). My goal is to create a query that can target the specific open vs done status of #1 vs #2 and associate those results to a dashboard. I am having a difficult time creating this query. 

The closest I have gotten on my own is similar to this: "Checklist Text[Paragraph]" ~ "Icons Installed" and "Checklist Content YAML[Paragraph]" !~ "Icons Installed checked: true status: done"

My problem is, even with specifying the YAML text, it does not appear to matter which box I complete. With that same filter, if I leave box #1 open and mark box #2 done that filter still believes it should drop off my filter which should not be the case. 

Any thoughts or advice? 

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