Attending as a freelancer/consultant--especially if speaking--or just for fun in a location you'd do a bunch of tourist stuff in anyway. Maybe, if you can get a free ticket (typically as a speaker). Or if it's low cost (i.e. no more than a few hundred $). But I wouldn't pay for a $1K+ ticket out of my own pocket.
I've done it here and there for cheaper conferences. I refer to them as my nerd vacations. But they're also far more targeted and more likely to have high quality talks, not the larger "trade show" type conferences.
Yep. I paid out of pocket to attend Handmade Seattle last fall and it was easily the best money I've spent - in spite of Handmade's emphases on systems and graphics programming both being pretty far outside my wheelhouse.
