I might do something like this.
Sub test()
Dim USBallCost As String

USBallCost = ""

Select Case itemmsgbox
Case "United States,youth ball team"
    USBallCost = "$197-$250"
Case "United States,teen ball team"
    USBallCost = "$250-$342"
End Select

If recommendation = "go for it" And itemmsgbox = "United States,youth ball team" Then
Worksheets(1).Range("Calculation").Value = USBallCost
End If

If recommendation = "larger need" And itemmesgbox = "United States,teen ball team" Then
Worksheets(1).Range("Calculation").Value = USBallCost
End If
End Sub