I think I figured it out - Job Name needs to be in the 1st field as it can only be linked to 1 WO #.
However, I’d still like help with question 2 if possible.

I’m trying to better understand what you mean; are you asking why in your 'Project Database’ there are those work orders showing up under the 'Dashboard’ field?

It looks pretty straightforward to me. Nothing appears broken. When you link a record from one table to a different record in another, the target table shows the reciprocal link. If you link from three records the first table to a single record in the second, the target record on the second table will show three links back to the first table, just like it does with your 45th & Lamar - 56 entry. That’s how Airtable operates.

You can still keep each WO’s details separate by adding all of that detail to the appropriate WO record. Each WO will have its own subcontractor, date(s), etc., but they’re all tied to the same project.

I’m not sure that I understand your second question. Could you provide a more specific example of what you’re doing, the results you’re seeing, and how those results differ from what you expect?