try this..this will give you what you want but if you are already separating from $ sign why dont you increment the counter there only
Dim FileReader = New StreamReader("D:\New Text Document.txt")
Dim line As String
Dim count As Integer
line = FileReader.ReadToEnd()
For Each alpha As Char In line
If alpha = "$" Then
count += 1
End If
Next
MessageBox.Show(count)