Its a painful dilemma for me. I have a few. They are great names which are totally out of reach in .com. However, when I actually start to get serious about building out a site I am reluctant to use anything except a dot com. I do think the proliferation of new extensions will gradually train people to type something besides "com" after the period, but it may take a while.
I know a guy (smart, educated) who still doesn't understand the difference between the address box and the search box on his browser ( still using Juno too )
My electrical engineer son tells me it typically takes 30 years between the time something is figured out in the lab until it is activly used in commercial applications. I have to wonder if that same rule of thumb might apply to domains.