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):
If you’re producing any kind of numbered items in-house that are multiple-up on a sheet where you need to control all the variables to meet your production needs, the autonumbering feature through numbered lists is the way to go! Just step and repeat away & InDesign will do all the work. No need to fool with a seperate “numbers” file or deal with a data merged document. I think it’s by far the best option for basic numbering.
 Does anybody have an easy way to set up sequential numbering in Coreldraw? Our shop has to lay out unit number plaques for vinyl cutting and sometimes my employee has to manually type in hundreds of numbers. I've read all the print merge suggestions for raffle tickets and such but I need the numbers entered into an object and not during the print process. 
The next step is to create the simple Excel workbook that contains the ticket numbers. Open a blank Excel sheet. Using Figure B as a guide, create the ticket numbering sheet and save it, making sure to note the new workbook's name and location. As we discussed earlier, the Excel workbook stores the ticket numbers. In this example, we'll create 11 tickets numbered 100 through 110. You'll need to update the ticket values for each merge.
If you start to type in what appears to be a numbered list, Word formats your manually typed "numbers" to an automatic numbered list. The main benefit of this option is that you do not need to click any button to start numbering and you can choose your numbering style as well. For example, if you type "(a) some text" and press Enter, it starts numbering using the "(a)" format.
Photograph of horn players taken at National Music Camp, Geelong Grammar, January 1993. I have no recollection of why all the horn players were wearing silly hats, but National Music Camp has a fine tradition of encouraging innocent pranks and general merriment—as well as damned hard work—so it's not entirely surprising. What's more puzzing is why I kept the photo all these years!
I wonder if I’m now up against a limitation of the feature: I have chapter numbers which are large and separated from the main text flow — each in its own text frame on the outer margin. These should be level 1 (‘X’) of the numbering system. Then the next heading (which is in the main body text flow) is level 2 (‘X.x’), and the next level 3 (‘X.x.x’). Unfortunately the level 2 headings do not follow from the level 1 numbering and I wonder if it’s because I’m using separate, non-linked frames for level 1? (The list does have ‘Continue Numbers across Stories’ checked.)
A single InDesign document can contain up to 9,999 pages, but page numbers can be as large as 999,999. (For example, you can correctly number a 100‑page document that starts on page 9,949.) By default, the first page is a recto (right) page numbered 1. Odd-numbered pages always appear on the right; if you use the Section Options command to change the first page number to an even number, the first page becomes a verso (left) page.
I find the numbered list feature to be completely confusing, even after reading Real World IDCS3. I just don’t seem to be able to wrap my brain around this feature…or maybe its just the dialogue box because the idea of list numbering makes perfect sense. I usually end up exhausting my vocabulary of not-very-nice words when I try to use this feature (and my vocabulary is fairly extensive).
My quick process involves setting up a row of plaques with a01, a02, a03, thru a09. Then copy the plaques to the clipboard. Run the REPLACE TEXT feature to replace "a" with "1". Move row down and paste clipboard back into page. Run REPLACE TEXT to replace "a" with "2". Repeat until I get all the numbers. It's faster than manually typing the numbers in but I know there's go to be someway of automating the process.
Numbering in Word is a bit of a nightmare at times and if you need multi-level numbering this could cause you much stress if you rely on the mouse alone. Using the keyboard to some degree makes this task very simple. I will explain how to create a multi-levelled numbered list and ask you to keep all the default formatting that Word gives you. This can be changed and modified but sometimes it messes up your layout. I advise to use what is there until you have the times and patience to master its intricacies.
12. To build the document, you will add the first merge field, the room number. To do this, choose Room from the Field list box, and click Insert Print Merge Field. This will place the variable on the document. Next, choose Subjectfrom the Field list box, and click Insert Print Merge Fieldonce more. Now both variables are inserted in the CorelDRAW document.
Determine what kind of numbering you want to use for your document or book. For long documents, you can assign chapter numbers. Each document can be assigned only one chapter number. If you want to use different numbering within a document, you can define ranges of pages as sections; these sections can be numbered differently. For example, the first ten pages of a document (the front matter) might use Roman numerals, and the rest of the document might use Arabic numerals.
Thanks for asking, but if you haven't done the Google search I suggested in post 1 of this thread and practiced with any of the tutorials at the linked resources there, or those recommended in posts 2 and 6, please do. Perhaps someone on the list will do the work you're requesting. As a trainer I feel my best value is to offer paths to solutions so folks can learn to use the tools. Some tools require more practice, but those are the ones that give the most pleasure of discovery at the "Aha!" moment that comes when one "gets it."
Numbering and Section options are available in the Pages Panel menu. These options allow you to define what page starts a section and how it should be numbered. A Current Page Number marker must be set on pages in order to use this feature. The Current Page Number is a special character inserted in a text frame on a page or master page (recommended) where the page number will appear, by selecting Type>Insert Special Character>Markers>Current Page Number.
@Aaron: I am stuck exactly with the same problem. I am constructing a style guide document, and thus my content is mainly images, not text. Still I do need numbered chapters in multiple levels, but the automatic numbering seems to be almost impossible as my headings are in separate text boxes. I have tried linking heading text areas, section markers, numbered lists and whatnot, but I am about to revert back to manual numbering instead of battling with this and wasting time! It’s just so devastating, I believe that machines should do what they do best, instead of people keeping track of numbering chapters!

Microsoft Publisher, the desktop publishing component of the Professional version of the Office Suite, can perform many time-saving tasks for busy business owners, including layout and design work. It can even help you avoid a shopping run to try to find tickets for your next employee picnic, holiday giveaway or executive board meeting. Create your own tickets, including the vital sequential ordering needed for raffles or attendance tracking, using Publisher’s page numbering. With a few tricky manipulations of the page number process, you can start running the numbers in an entirely new fashion.
×