The shipping quote server behaviors will not work this way by default. How the server behaviors work is to interact with the shipping quote server go get a quote based on the values you have specified. When the quote is retrieved it is stored in a session variable. It is this session variable that is used for the shipping charge for that particular rule, so it is designed to work with only a single quote per order and provider.
If you had two of the shipping quote server behaviors on the page and managed to set them to save the value in different session variables you could implement the shipping like you have described. This would be a custom process though and it would force you to update the source code for the shipping quotes to make it all work. If it is something that you feel up to you should give it a try, but you will need to know some basic php coding and how to deal with session variables.