Ok, let me try to explain what is happening here...

Steemit allows us to use Markdown Syntax for creating and editing posts. Markdown can be used to write HTML in an easier/shorter way.

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For example:

The HTML:
<h2>Big Header</h2>
can be achieved with Markdown by just typing:
## Big Header

When you type 1) or 1. followed by a space, the editor converts the Markdown to HTML, so that it will result in an ordered list <ol> as shown here:

<ol>
   <li>First</li>
   <li>Second</li>
   <li>Third</li>
</ol>

1. First
2. Second
3. Third

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The editor will exit an opened list as soon as more than one line break occurs, because it can't know, if the following lines should be added to the previous <li> (list item) or not. The next 2) creates a new list, therefore the numeration starts again from 1.

There are different ways to circumvent that behaviour:

• Use <br> instead of normal line breaks inside the list
• Use HTML ordered list as shown above
• Use 1.  to prevent creating a HTML list (indentation will not work then)

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Hope this helps to better understand how that all works internally ;)