The values of a command button determined by other userforms values

Hello all!

So, I have a workbook that has the following items:

A command button to open a userform with multiple checkbox items to select. The selections are assigned a numerical value and are then summed to display a specific message in a cell.

A command button to open another userform with two comboboxes in which the selected values (one one selection is permitted per combobox) are then displayed in a specific cell seperated by comma

A final command button to make a specific calculation based on the values listed in the cells from the above command boxes

What I cant seem to do is get the final command button to display the calculation:

Private Sub CalculateButton_Click()

If "recommendation" = "go for it" And "itemmsgbox" = "United States,youth ball team" Then
Worksheets(1).Range("Calculation").Value = "$197-$250"
End If
If "recommendation" = "larger need" And "itemmesgbox" = "United States,teen ball team" Then
Worksheets(1).Range("Calculation").Value = "$250-$342"
End If

and so on and so on for a few hundred more variables.
End Sub

When I hit the calculate button nothing displays in the box. Am I missing an execution?