Are convention and propriety always the right way to go?  Are unconvention and impropriety always a negative?

There is no perfect answer, but I know the chance you never take is surely unrewarding.  If you don't try you will never know.  

If there is something you want or need, there is no harm in politely asking for it and, oft times, you might be pleasantly surprised by the response.  I can still hear my father counseling "There is no harm in asking!"

There is no benefit, in such circumstances, in being shy, polite or timid. 

Let them label you aggressive.  Go for it!

PS: Dare to be great!