This is not something I've dabbled with before but I am getting the same behaviour as you in Word 2013 and don't know if it was different in earlier versions.
In any case, perhaps you need to use a macro to create a new ListTemplate each time you need to jump.
Code:
Sub Macro3()
Dim aLT As ListTemplate
Set aLT = ActiveDocument.ListTemplates.Add(OutlineNumbered:=True)
With aLT.ListLevels(1)
.NumberFormat = "%1."
.TrailingCharacter = wdTrailingTab
.NumberStyle = wdListNumberStyleArabic
.NumberPosition = CentimetersToPoints(0)
.Alignment = wdListLevelAlignLeft
.TextPosition = CentimetersToPoints(1)
.TabPosition = CentimetersToPoints(1)
.ResetOnHigher = 0
.StartAt = InputBox("Start where?", "Re-Start Me Up", 9)
.LinkedStyle = ""
End With
Selection.Range.ListFormat.ApplyListTemplateWithLevel ListTemplate:=aLT, _
ContinuePreviousList:=False, ApplyTo:=wdListApplyToThisPointForward, _
DefaultListBehavior:=wdWord10ListBehavior
End Sub
Once you have done this to a list, if you want to add a second break, press Ctrl-Q to reset the paragraph(s) and then run the macro again.