The board is not operating properly, cannot find or reply to your request to:
select column, count & report items in it, move to next column based on user
choice and repeat - but here is code that I believe will do what you want. I
hope so, and I hope you see this message.

Sub CountEntriesInAColumn()
Dim lastUsedColumn As Long
Dim lastUsedRow As Long
Dim currentColumnArea As Range
Dim itemCount As Long
Dim continueFlag As Integer

lastUsedColumn = ActiveCell.SpecialCells(xlLastCell).Column
lastUsedRow = ActiveCell.SpecialCells(xlLastCell).Row
continueFlag = vbYes ' initialize
Do While continueFlag = vbYes
Cells(1, ActiveCell.Column).Activate
Set currentColumnArea = _
ActiveSheet.Range(ActiveCell.Address & ":" & _
Cells(lastUsedRow, ActiveCell.Column).Address)
itemCount = Application.WorksheetFunction. _
CountA(currentColumnArea)
'test if this is the last column
If ActiveCell.Column = lastUsedColumn Then
'either at last used column or to the right of it
MsgBox "This column has " & _
itemCount & " entries in it." & vbCrLf _
& "It is the last used column.", vbOKOnly, _
"Column Entry Count"
continueFlag = vbNo ' set flag to stop loop
Else
'more columns to examine
continueFlag = MsgBox("This column has " & _
itemCount & " entries in it." & vbCrLf _
& "Do you want to continue?", vbYesNo, _
"Column Entry Count")
If continueFlag = vbYes Then
'move to next column
ActiveCell.Offset(0, 1).Activate
End If
End If
Loop
MsgBox "Operation Complete"
End Sub