I arrived at a limited form of the results you want using the following code
Code
Sub MultiEntryCell()
Dim myDate As Date
Dim myPhase As String
Dim myPM As String
Dim myPM2 As String
Dim myPM3 As String
Dim myPM4 As String
Dim myLocation As String
Dim myLocation2 As String
Dim myLocation3 As String
Dim myLocation4 As String
Dim myRange As Range
Dim myRange2 As Range
Dim i As Integer
Dim j As Integer
ActiveCell.FormulaR1C1 = "=COUNTIF(Data!RC:R[16]C,R[1]C)"
j = ActiveCell
i = 1
ActiveCell.Offset(1, 0).Select
myDate = ActiveCell
myPhase = Range("A3")
Range("C3").Select
Set myRange = ActiveCell
Sheets("Data").Select
Range(myPhase).Select
Selection.End(xlUp).Select
Range(Selection, Selection.End(xlDown)).Select
For i = 1 To j
Selection.Find(what:=myDate, after:=ActiveCell, LookIn:=xlFormulas _
, lookat:=xlPart, searchorder:=xlByRows, searchdirection:=xlNext, _
MatchCase:=False).Activate
If i = 1 Then
Set myRange2 = ActiveCell
ActiveCell.Offset(0, -2).Select
myPM = ActiveCell
ActiveCell.Offset(0, 1).Select
myLocation = ActiveCell
Application.Goto myRange2
Range(Selection, Selection.End(xlDown)).Select
End If
If i = 2 Then
Set myRange2 = ActiveCell
ActiveCell.Offset(0, -2).Select
myPM2 = ActiveCell
ActiveCell.Offset(0, 1).Select
myLocation2 = ActiveCell
Application.Goto myRange2
Range(Selection, Selection.End(xlDown)).Select
End If
If i = 3 Then
Set myRange2 = ActiveCell
ActiveCell.Offset(0, -2).Select
myPM3 = ActiveCell
ActiveCell.Offset(0, 1).Select
myLocation3 = ActiveCell
Application.Goto myRange2
Range(Selection, Selection.End(xlDown)).Select
End If
If i = 4 Then
Set myRange2 = ActiveCell
ActiveCell.Offset(0, -2).Select
myPM4 = ActiveCell
ActiveCell.Offset(0, 1).Select
myLocation4 = ActiveCell
Application.Goto myRange2
Range(Selection, Selection.End(xlDown)).Select
End If
'i = i + 1
Next i
Application.Goto myRange
ActiveCell = myPM & " " & "in" & " " & myLocation & Chr(10) _
& myPM2 & " " & "in" & " " & myLocation2 & Chr(10) _
& myPM3 & " " & "in" & " " & myLocation3 & Chr(10) _
& myPM4 & " " & "in" & " " & myLocation4
End Sub
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I have short cut the finding and allocating months and phases but maybe there is something you can use.