I know that PrintShopMail will do it, but I was wandering if there was a less expensive solution out there so that I could get numbered tickets (usually 4-up) right off the Xerox. I just want to avoid having to go the the Windmill after trimming and doing it the old fashion way. There is a tiny little copy shop here in town that is doing it, and am willing to bet that they are not using PrintShopMail, but I'm also not going to ask them to share their methods with a competitor. There has to be cheaper solution. I know that I can do it with auto page numbering in Indesign, but that means I can only print raffle tickets 1-up which wont work.
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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.

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.

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.)
I’m not sure which version of InDesign first introduced printing Thumbnails like this, but even if yours doesn’t support that, your printer driver may have a similar feature of its own. Check the printer’s own dialog box by clicking “Setup…” near the bottom left corner of the Print dialog and dismissing the warning, then clicking “Preferences…” in Windows’s Print dialog that comes up (I’m not sure how to access this on Mac OS X, but I’m pretty sure there’s an easy way). For instance, on many HP printers, the feature you want is called “Pages per sheet” and has a drop-down offering 1, 2, 4, 9, or 16 pages per sheet.
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):
In the Adobe InDesign document I’m working on here we actually have two master pages, an ‘A’ master and a ‘B’ master so I’m going to select both the left and right hand page frames with the special character in on my ‘A’ master and go to Edit>Copy. I’m then going to double click on my ‘B’ master page and go to Edit>Paste in place. this will then copy the special character and position it in exactly the same place as it appears on my ‘A’ master.

If the list you want is as simple as "1", "2", "3", you'll appreciate how easy it is to apply this type of numbering in legal documents. Simple numbered lists are different in Word 2000 than they were in Word 97. In Word 2000, the default for even the most basic list is multi-level. For example, if you number an item and press Enter and then press the TAB key, Word automatically formats this number as the second level in an outline numbered list format. Single and multi-level numbering are explained later in this chapter.
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.
@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!
The values for Number position (here called Aligned at), Text indent and Follow number with are in the Position section at the bottom. With multi-level numbering, you also have easy access to settings that control the type of numbering at each level, the characters before and after each level’s numbers (period versus parenthesis), and the list number style (1, a, I, etc.).
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.