There are lots of options. For instance, you might reduce the amount of space between the number and the text by changing the Text indent at setting. Or, you might center the heading by choosing Center from the Number alignment dropdown. For even more options, click More to expose several more settings. You could use the Apply changes to option when setting level 1 to the I, II, III numbering style instead of changing it for each level.

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.

Word automatically formats text as a numbered list when you when you type a number and a period followed by a space: Word adds a tab and creates a ¼-inch hanging indent. (If the paragraphs already have hanging indents, the original settings are preserved.) The quickest way to create a custom numbered list is to change the formatting of an existing (or automatically created) list.
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).
Running captions number figures, tables, and other items consecutively in a document. For example, the first figure caption starts with the words “Figure 1,” the second with “Figure 2,” and so on. To make sure that figures, tables, or similar items are numbered consecutively, define a list for the item, and then create a paragraph style that includes the list definition. You can also add descriptive words such as “Figure” or “Table” to the numbering scheme of the paragraph style.
A multi-level list is a list that describes hierarchical relationships between the list paragraphs. These lists are also called outline lists because they resemble outlines. The list’s numbering scheme (as well as indentations) show rank as well as how items are subordinate to one another. You can tell where each paragraph fits in the list with respect to the paragraphs before and after it. You can include up to nine levels in a multi-level list.

When the “Current Page Number” placeholder sits on a master page, every page to which you assigned that specific master page will display this variable – the number will change automatically on every page. If you change the style assigned to the placeholder on the master page (let’s say you set it to bold), all page numbers will update to that style (all numbers will become bold).

InDesign allows you to add a page number marker to a master page within the document. The master page functions as a template for every page it's applied to, so the consecutive page numbers appear on every page. InDesign updates the page number automatically as you insert, delete and move pages. To add a page number marker to a master page, create a text box on the master page by going to the Type menu and choosing "Insert Special Character," "Markers" and then "Current Page Number."

By default, bullets and numbers inherit some of their text formatting from the first character in the paragraph to which they’re attached. If the first character in one paragraph is different from the first characters in other paragraphs, the numbering or bullet character may appear inconsistent with the other list items. If this is not the formatting you desire, create a character style for numbers or bullets and apply it to your list by using the Bullets And Numbering dialog box.

Thanks David for posting this for me. And thanks for sending me the .inx fie. I had a complete memory lapse on how to make a number list like that and was uber-cofused. If it was written about before I couldn’t find it on the search function for the site. And even if it is over a year old it’s still good info. It is in the Mailbag section so it really was just an answer to an email and generoulsy posted.
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 for a good entry level package
The software Classic Menu for Office is designed for the people who are accustomed to the old interface of Microsoft Office 2003, XP (2002) and 2000. It brings back the classic menus and toolbars to Microsoft Office (includes Word) 2007, 2010, 2013 and 2016. The classic view helps the people to smoothly upgrade to the latest version of Office, and work with Office 2007/2010/2013/2016 as if it were Office 2003 (and 2002, 2000).

See Word's Numbering Explained by John McGhie, MVP - comprehensive and not pretty (Downloadable pdf file in letter size) - Reading this is vital to anyone attempting to use automatic numbering or bullets in a law office setting or other places where the documents are likely to be reused or heavily edited. See also How to Create a Template with a downloadable template with style-based numbering.
This feature is easiest to use when you combine it with Word's built-in heading styles. However, you can map a custom heading style to the multilevel numbering feature—it just takes more work. Word handles nine levels, but any document with more than four levels should receive a serious developmental edit. More than four becomes confusing and perhaps worse, unreadable.
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In bulleted lists, each paragraph begins with a bullet character. In numbered lists, each paragraph begins with an expression that includes a number or letter and a separator such as a period or parenthesis. The numbers in a numbered list are updated automatically when you add or remove paragraphs in the list. You can change the type of bullet or numbering style, the separator, the font attributes and character styles, and the type and amount of indent spacing.

Tip  Follow the same steps (above) to create Request for Production or Request for Admissions. The only difference would be in Step 3, you would change the "rog" to "rpf" or "rfa". This will keep unique numbering schemes running in the same document. Therefore, you could have an Interrogatory No.1 as well as Request for Production No.1. Keep in mind that if you cut, copy or paste sequence codes, you'll need to select them and press F9 to update the field codes. They do not update automatically.

Drag the number, which Publisher defaults to “1,” into place on the ticket. To change the sequence, such as to start with “100” instead of “1,” click the “Page Number” button again and choose “Format Page Numbers.” Click the “Start this section with” radio button and type the new number into the field. Click the “OK” button to have Publisher update the ticket number.