1) I'm really no fan of VLOOKUP(). INDEX/MATCH is the most robust of all lookup tools, it only takes a little more time to get used to reading, and once you do, it works for anything. It replaces LOOKUP, VLOOKUP and HLOOKUP and suffers from none of the limitations they have.
Q5: =IF(ISNUMBER(MATCH($N5, 'Actual Logins'!$A:$A, 0)), INDEX('Actual Logins'!C:C, MATCH($N5, 'Actual Logins'!$A:$A, 0)), "")
Copy that down the Q column and across to the R column and you're good to go on that.
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I looked at the macros in your sheet, the macro in Module 2 doesn't belong there and won't work from there.
To use a Worksheet_Change macro, you have to put that in the sheet module where you want that to be active. So move that into the sheet itself, you'll find them listed in the VBAProject above the modules.
I typically give global permission to Excel to make changes with macros even though I've protected the sheets from USERs making changes. The easiest way to do that is with a workbook_open macro stored in the ThisWorkbook module or a Worksheet_Activate macro in the sheet module.
In ThisWorkbook:
In the Sheet module:
If you wanted to put the permissions part in the sheet, too, instead of Thisworkbook, then this version will work in the sheet module:
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