Org is great at handling plain lists - see the section about plain lists in the manual. This small screencast demonstrates a few things you can do with them. This is with GNU Emacs 23.0.94.2 and Org 6.27trans.

Here is the list of features I demonstrate:

• convert a plain list from itemize to numbered
• re-order the items in this list
• show how numbers are automagically updated
• add a checkbox to some items of the list
• add a [ ] cookie to the headline above and update it
• replace the [ ] cookie with a [%] and update it
• export the list contained in the region into HTML

The good news is that all these features are also available in other mode like message-mode, thanks to the orgstruct-mode minor mode (see the manual about orgstruct-mode.)