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):

Do not let me lead you into a headache under false pretences: this FAQ is not going to tell you how to fix a document that contains broken numbering. It simply explains how the numbering works: this is valuable information if you work with Word a lot, and by understanding it, you can often work out how to fix a document. However, this FAQ is not going to tell you how.  (For a discussion of methods, see: List Restart Methods).
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Defined lists are often used to track paragraphs for numbering purposes. When you create a paragraph style for numbering, you can assign the style to a defined list, and paragraphs are numbered in that style according to where they appear in the defined list. The first paragraph to appear is given number 1 (“Table 1”), for example, and the next paragraph is given number 2 (“Table 2”), even if it appears several pages later. Because both paragraphs belong to the same defined list, they can be numbered consecutively no matter how far apart they are in the document or book.
CK Note: Word 2007 - 2013 interface has an different automatic numbering scheme which I have been told is much less subject to corruption. Microsoft Word 2010 Bible by Herb Tyson, MVP. However numbering is still very imperfect in these later versions. I still recommend following Shauna Kelly's step-by-step instructions (see above) if setting up numbering in a template or in a document likely to be heavily edited. If you start without doing this and end up with "spaghetti numbering," fixing it will be a very large chore!

In the example I explained, I was using a list, but did it with un-linked text boxes using “continue from previous number” and “continue numbers across stories.” I’m guessing that there is no way to tell InDesign that even though there are 4 text boxes on the page, that there are two different lists? I’d probably have to just create two threaded stories for that scenario to work.
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. numbering using coreldraw
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