The values of a command button determined by other userforms values

You are treating the variable names as literal strings.

Try

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