I'm not an expert but you could set the protection on the comments cell to unlocked. Then protect the sheet so only unlocked cells can be selected.
Then have a userform (UserForm1) with a text box and 2 command buttons. Set the ControlSource property of the textbox to the reference of the comments cell. In the code below, B5 is the comments cell.
Then the two command buttons can be one for "Enter" and one for "Cancel"
The "Enter" Command Button Could then have the code:
The Cancel Button Could Have
As for the date issue. Then you could create a workbook_open event to check if a deadline has passed and protect the comments cell if it has....
Then simply put a button next to the comments box (B5) and assign a macro with a single line of vba
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