orschiro the markdown list syntax doesn't care what number you put at the beginning of a line, you can use any number and it will be converted to an "ordered list" which the browser will number automatically.
Input:
1. first
1. second
1. third
Output:
- first
- second
- third
For this reason the "numbered list" formatting control in our editor was made the simplest way possible, it just inserts the number one again and again.
EDIT: as to why the list doesn't continue automatically when you enter a newline: we used to have that feature but the library that implemented it was causing too many issues and had to be removed. If someone can re-implement the auto-newline behavior in plain javascript we might re-add it. Currently you need to type the number for the next line manually. All formatting controls are one-time inputs.
What you can do is write every item of the list first without any number, then select all lines and click the list format button. Then all lines will be numbered at once.
