My number and numeral lists aren't lining up

The key is to carefully set up numbering associated with styles. The resources by John Korchok at https://www.brandwares.com/bestpractices/2016/06/outline-numbering-in-word-for-os-x/ apply to Word for Mac, specifically.

For more information on this, see Number Alignment by Suzanne Barnhill, MVP.

You must set the tabs and indents in the Define New Multilevel List dialog

Joseph,

I feel your pain. The built-in bulleted and numbered lists that Microsoft supplies are horrendously formatted and fixing them is not a walk in the sun.

My advise is to stop trying and create you own Custom List Style that meets your requirements. The basic steps are contained here:
https://shaunakelly.com/word/numbering/numbering20072010.html

Alternately, you can copy the following code to a standard VB code module. Run (or modify and run) Create_EditMultiLevelListStyle to set up a Custom List Style on the fly:

Option Explicit
'Note - change names to suit.
Private Const m_strListStyleName As String = "My ML Numbered List"
Private Const m_strStyleLevelPrefixName As String = "CustLL"
'Note - change the global indent value to suit.  Value is in points e.g., half inch is 36 points.
Private Const m_lngIndent As Long = 21

Sub Create_EditMultiLevelListStyle()
Dim oListStyle As Style
Dim oStyle As Style
Dim oLL As ListLevel
Dim oLL1 As ListLevel

Dim lngPoints As Long, lngLevelIndex As Long
Dim bUpdate As Boolean
  'I created this VBA procedure because I think the built-in multilevel lists (MLL) in Word look absolutely stupid.  I realize that is
  'a broad brush statement for out of 6 plus billion souls out there, some may feel the look of the MLL list this procedure creates is even worse.
  'Here we are. If you like something else, you can make adjustments in the code.
  'I don't normally comment code heavily but make an exception here as I want any potential user to understand the mechanics and what is going on.
  'Perhaps some smart guy or gal out there will jump in with suggestions for improvement, explainations or fixes.
  'The primary goals of this code are to:
    'a) Produce a MML that is linked to 9 different paragraphs styles (one for each list level)
    'b) Produce a MML that has a unique list member index for each list level
    'c) Produce a MML with "lesser" yet consistent indents than the built-in MML provided with Word
  bUpdate = True
  On Error Resume Next
  'Get (or since it won't exist initially, create) the named list style.
  'I like to use a "Named" list style, because I will then know what it is when I see it in the gallery.
  Set oListStyle = ActiveDocument.Styles(m_strListStyleName)
  If Err.Number <> 0 Then
    'If the named list style didn't exists then we create it now.
    Set oListStyle = ActiveDocument.Styles.Add(m_strListStyleName, wdStyleTypeList)
    bUpdate = False
  End If
  DoEvents
  'Initialize the indent value. The indent value determines how far from the left margin the index number appears.
  lngPoints = 0
  On Error GoTo 0
  'Define the ListTemplate associated with the list style.
  With oListStyle.ListTemplate
    For lngLevelIndex = 1 To 9
      'Global actions for all nine list levels
      Set oLL = .ListLevels(lngLevelIndex)
      oLL.Alignment = wdListLevelAlignLeft
      'Initialized text position. The hanging indent.
      oLL.TextPosition = 0
      'Note - the value of lngPoints is increased by the value you set with the constant m_lngIndent with each iteration of the this For ... Next loop
      oLL.NumberPosition = lngPoints
      oLL.TabPosition = lngPoints + m_lngIndent
      oLL.TrailingCharacter = wdTrailingTab
      oLL.ResetOnHigher = True
      'Link the list level to a unique paragraph style. Note - If that style doesn't exists, we create it with the error handler.
      Select Case lngLevelIndex
        Case 1
          Set oStyle = ActiveDocument.Styles("List Number")
          oLL.LinkedStyle = oStyle.NameLocal
        Case 2 To 5
          Set oStyle = ActiveDocument.Styles("List Number " & lngLevelIndex)
          oLL.LinkedStyle = oStyle.NameLocal
        Case Else
          On Error GoTo Err_Style
          Set oStyle = ActiveDocument.Styles(m_strStyleLevelPrefixName & lngLevelIndex)
          oLL.LinkedStyle = oStyle.NameLocal
          On Error GoTo 0
      End Select
      Select Case lngLevelIndex
        Case 1
          'Note - for levels 1 - 3, I want my second line text to align under list member number/letter
          'To align under first character of list member text, append + m_lngIndent to .Text Position line.
          oLL.TextPosition = lngPoints '+ m_lngIndent
          Set oLL1 = oLL
          oLL.NumberFormat = "%1."
          oLL.NumberStyle = wdListNumberStyleArabic
        Case 2
          oLL.TextPosition = lngPoints  '+ m_lngIndent
          oLL.NumberFormat = "%2."
          oLL.NumberStyle = wdListNumberStyleUppercaseLetter
        Case 3
          oLL.TextPosition = lngPoints '+ m_lngIndent
          oLL.NumberFormat = "%3)"
          oLL.NumberStyle = wdListNumberStyleArabic
        Case 4
          oLL.TextPosition = lngPoints + m_lngIndent
          oLL.NumberFormat = "%4."
          oLL.NumberStyle = wdListNumberStyleLowercaseLetter
        Case 5
          oLL.TextPosition = lngPoints + m_lngIndent
          oLL.NumberFormat = "%5."
          oLL.NumberStyle = wdListNumberStyleArabic
          oLL.Font.Underline = wdUnderlineSingle
        Case 6
          oLL.TextPosition = lngPoints + m_lngIndent
          oLL.NumberFormat = "%6)"
          oLL.NumberStyle = wdListNumberStyleLowercaseLetter
        Case 7
          oLL.TextPosition = lngPoints + m_lngIndent
          oLL.NumberFormat = "%7]"
          oLL.NumberStyle = wdListNumberStyleArabic
        Case 8
          oLL.TextPosition = lngPoints + m_lngIndent
          oLL.NumberFormat = "%8."
          oLL.NumberStyle = wdListNumberStyleLowercaseLetter
          oLL.Font.Underline = wdUnderlineSingle
        Case 9
          oLL.TextPosition = lngPoints + m_lngIndent
      End Select
      lngPoints = lngPoints + m_lngIndent
    Next lngLevelIndex
  End With
  If bUpdate Then
    MsgBox "Defined changes to list and associated linked paragraph styles are completed.", vbInformation + vbOKOnly, "REPORT"
  Else
    MsgBox "This list style and associated linked paragraph styles have been created." & vbCr + vbCr _
      & "To reflect changes in the List Styles gallery please save, close and reopen the template file.", vbInformation + vbOKOnly, "REPORT"
      'Does anyone know how to force the List Styles gallery to refresh with code?
    Selection.Paragraphs(1).Style = "List Number"
  End If
  '***
lbl_Exit:
  Exit Sub
Err_Style:
  Select Case Err.Number
    Case 5941
      'Create a unique paragraph style to serve as the linked paragraph for the indexed level.
      Set oStyle = ActiveDocument.Styles.Add(m_strStyleLevelPrefixName & lngLevelIndex, wdStyleTypeParagraph)
      oStyle.BaseStyle = "List Paragraph"
      Select Case lngLevelIndex
        Case 4 To 9
          'I specifically don't want additional white space after levels 4 through 9.  You can adjust this to suit your own taste.
          oStyle.NoSpaceBetweenParagraphsOfSameStyle = True
      End Select
    Case Else
      MsgBox Err.Number & " - " & Err.Description
  End Select
  Resume
End Sub
Sub DeleteStyleSet()
'Use this procedure to remove the list and associated linked paragraph styles.
'You should save and close the template, then reopen to reset the List Styles Gallery content.
Dim oStyle As Style
  For Each oStyle In ActiveDocument.Styles
    If oStyle.NameLocal Like m_strStyleLevelPrefixName & "*" Or oStyle.NameLocal = m_strListStyleName Then
      oStyle.Delete
    End If
  Next
End Sub