I have posted the script below that will send out an email notification with attachments when the user defined field is populated with the value 'In Progress'. The body of the email will contain the Cycle ID number, as well as the project name where the cycle is located. You will need to edit the script to work with your current environment. I also recommend that you test this in a test project before implementing into your production environment.
Add this workflow to the existing Cycle_FieldChange(FieldName) subroutine:
    Sub Cycle_FieldChange(FieldName)
      'On Error Resume Next
         Dim strSubject, strDes, strComment
         Dim objTDC, objAttachFact, objAttachment, objAttachment2, objAttachList
         Dim objCycleFact, strCycleId, objCycle, objAttachmentList
         Set tdc = TDConnection
         Set objTDC = TDConnection
         Set objCycleFact = objTDC.CycleFactory
         strCycleId = Cycle_Fields(''RCYC_ID'').Value
         Set objCycle = objCycleFact.Item(strCycleId)
         Set objAttachFact = objCycle.Attachments
         Set objAttachList = objAttachFact.NewList('''')
         For Each objAttachment In objAttachList
            If Instr(objAttachment.ServerFileName, strFilterType) then
                j = j + 1
            End If
         Next
         If j < 1 Then
    
         Else
    
           ReDim objAttachmentList(j - 1)
         End If
    
         For Each objAttachment2 In objAttachList
            If instr(objAttachment2.ServerFileName,strFilterType) Then
                objAttachmentList(i) = objAttachment2.ServerFileName
                i = i + 1
            End If
         Next
    
         'Replace 'RCYC_USER_01' with the title of the user defined field
         If Cycle_Fields.Field(''RCYC_USER_01'').Value = ''In Progress'' Then 'This line used if specific value needs to be used
         strSubject = ''Status Change Notification for Cycle #'' & Cycle_Fields.Field(''RCYC_ID'').Value & '' in project '' & tdc.ProjectName
         strDes = ''The status for Cycle # ['' & Cycle_Fields.Field(''RCYC_ID'').Value & ''] has changed to [ '' & Cycle_Fields.Field(''RCYC_USER_01'').Value & '' ].'' &_
         '' Any documents attached to Cycle # ['' & Cycle_Fields.Field(''RCYC_ID'').Value & ''] have been attached to this email. ''
         'the next line sends an email to a single user - multiple users need to be inserted in the quotes separated by semi-colons
         tdc.SendMail ''your_email@alm_mail.com'', '''', strSubject, strDes, objAttachmentList
         Set TDConnection = nothing
         End If
      'On Error GoTo 0
    End Sub