One pain point I've had since switching from Basic Auth has the lack of debugging via a terminal and curl. That was pretty useful.
For Ruby-minded folks there's http://github.com/marcel/twurl which is effectively curl that uses OAuth - though it isn't the same.
John Nunemaker wrote a tutorial on how to get get up and running with OAuth pretty quickly (though it is for the Ruby/Rails audience) http://railstips.org/blog/archives/2009/03/29/oauth-explaine... .
I'll admit getting started with OAuth takes some time to ramp up at first, but that ramp up time gets smaller each subsequent app.