You can define a section prefix to label section pages automatically. For example, if you specify A– for Section Prefix on page 16 of a document and include the section prefix, the page will appear in the table of contents or index as A–16. Text you type for a section marker appears when you choose Type > Insert Special Character > Markers > Section Marker.
You can't use Word's Numbering feature to generate a multilevel numbering system, even if you use built-in heading styles. Figure A shows a document with two styled heading levels: Heading 1 and Heading 2. You can apply the Numbering option (in the Paragraph group) and Word will number the headings consequently, but the feature ignores different levels; if you expected 1, 1.1, 2, 2.1, and 2.2, you might be surprised. If you select the entire document first, Numbering not only ignores the different levels, but it also numbers the paragraphs!

A CorelDRAW Graphics Suite expert, Roger has been a popular presenter at industry trade shows. He has developed and conducted classroom training and online sessions throughout North America and has authored articles for key industry magazines, including SQE Professional and The Screen Printers Resource Guide, and is a regular contributor to Trophex magazine. You can train with Roger using his book, Bring It Home with CorelDRAW: A Guide to In-House Graphic Design, or by watching his online course, CorelDRAW Essential Training.
Another fan of Fusion Pro Desktop here. This is exactly what you need. We have sold both PrintShop Mail and Fusion Pro Desktop for this very application (numbering) and other VDP applications. Fusion Pro Desktop easily beats PrintShop Mail from both a price and performance viewpoint. You could also try Printer's Bench http://www.elkriversystems.com/ProductsList.aspx for a good entry level package
One of the harder things to do in Adobe InDesign, surprisingly for a page layout tool, is to create multilevel or outline format numbered lists.  The right way to accomplish this, according to the folks at Adobe, is to create a Style for every level of the list you’d like to have! Here are Adobe’s instructions on how to do so (This content is taken directly from https://helpx.adobe.com/indesign/using/bullets-numbering.html#create_multi_level_lists):

GREAT tip with lots of uses! Thank you. This will save me hours of work on some tickets I’m designing. However, I also need to set up table tents that have numbers on them. They’re 2-up, and are folded, so each number needs to appear twice on the same page. In short, I want a page with 1/1 and 2/2, and I’m getting 1/2 and 3/4. Am I missing an obvious fix? Thank you.
Note  If TAB and SHIFT+TAB do not work for changing the indents for outline numbering, you probably have the option Tabs and Backspace set left Indent turned off. To change this setting, from the Tools menu, choose Options. Select the Edit tab and check the option Tabs and backspace set left indent. As an alternative to turning this option on, you can instead use ALT+SHIFT+LEFT ARROW or RIGHT ARROW to increase or decrease outline numbering.
A defined list can be interrupted by other paragraphs and lists, and can span different stories and different documents in a book. For example, use defined lists to create a multi-level outline, or to create a running list of numbered table names throughout your document. You can also define lists for separately numbered or bulleted items that are mixed together. For example, in a list of questions and answers, define one list for numbering the questions and another for numbering the answers.
And what all did I forget to do? I forgot to go to 'Styles', 'Paragraph Styles', and I went, right click 'Redefine' because I've reverted to what it was before. So that's page numbering, we used A, B, C, D at the beginning. And we're going to use 1, 2, 3, 4, 5 for the rest of it. The only trouble happens, is when you go 'File', 'Print' now, and you're like, "Hmm." "I want to print pages." and you're not too sure. So what I have to do is go to A, through to 30. So it will include A, B, C, D, E, and all the way through the numbers. What if I just need A, B, or if I just print 1-30? It's going to skip out these first pages. That's just something to be aware of when you're printing, or making PDFs, that the page numbering is a little bit stranger now that we've gone and messed around with the page numbering.
You can add many of these items by using text variables. InDesign includes several preset variables, such as Creation Date and File Name. You can modify these variables, and you can create your own. For example, you can create a variable that displays the first use of a Heading paragraph style in the header or footer. Once you create or edit the variables you need, you assemble them on the master page to create your header and footer, and then you apply the master page to the appropriate document pages.
Changing the numbering display affects how pages are indicated in the InDesign document, as in the Pages panel and in the page box at the bottom of a document window. The numbering display also affects how you specify page ranges when printing and exporting the document. However, the numbering display does not change the appearance of page numbers on document pages. numbering in indesign
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