I personally question whether having the chat system auto correct our numbering is overall beneficial or not...
I had this issue in an early conversation.. someone had began a list and I continued it.. and it made my 4. into a 1. which made it incorrect...
also assume a situation similar to Impaller vs the world.. where one person lists multiple posibilities.. if you put up "4. because blah blah blah" it would come up as "1. because blah blah blah"
I would consider putting this as a uservoice, but I'm fairly certain that it isn't as pressing an issue as many of the things already on there. and would be dissapointed to see votes put into it.. so instead hopefully Fizzer will see this post/conversation and decide to do it on his own.. ;)
/rant.off