So now I'm trying to examine your HeaderOutlineTitle function... and there are a few bits I don't get, and a few bits I think you can improve the logic of.

So a couple of comments:
1. Don't use single line If...Then statements. There is zero optimization to this, and it essentially means you can't effectively break point it.
2. IIF constructs are not appreciably faster (to my knowledge), and they are much more confusing to read and troubleshoot.
3. Complex And/Or operations are likewise difficult to troubleshoot... for example.
[vba]
'If it's blank or a number or a period, exit
If tCH= " " Or (Not IsNumeric(tCh) And tCH <> ".") Then
Exit For
End If
[/vba] That logic test doesn't make a lick of sense to me. Especially with the inaccurate comment. What you are literally testing there is
A. If it is a blank space OR
B. It is NOT a number AND it is NOT a period.

So, basically... you have some valid characters to allow you to keep processing, right? This is an excellent time to make use of Select Case, for multiple reasons. It's easier to modify, and it's easier to understand. For example...
[vba]
Select Case tCH
Case 0 to 9, "."
'acceptable, keep processing
Case Else
Exit For
End Select
[/vba] You don't have to use the 0 to 9 construct, you could do "0", "1", "2", etc... but Select Case is often a good way to do an acceptable list. It's certainly easier to read and modify than a complicated If statement utilizing AND/OR operators.

4. IIF... blech. Easier to read this way...
[VBA]
'If this is a number, keep track, otherwise reset the counter
If IsNumeric(tCH) Then
NumberCounter = NumberCounter + 1
Else
NumberCounter = 0
End If
[/VBA]
I would be surprised if the above simplifications changed the over all processing time.

As a benchmark, running my code on your 4 meg document took around 2 minutes, with the majority of that time being putting stuff into the word table (which may very well be faster for you, since excel doesn't have to re-paginate periodically when large amounts of data are put into a spreadsheet.

I think there are ways to simplify what you want out of the HeaderOutlineTitle functionality even without going into Wildcard searching.

But if you want to investigate that, it's probably worth of its own post -- something along the lines of "How can I use wildcard searching to match..."
And then list out all the patterns that you want to find, coupled with the kinds of patterns you don't want to match, and perhaps one of our resident expert wildcard searchers will weigh in.