"Is it OK to depart VFR and pick up my IFR clearance in the air? I've heard different opinions on this." - Peter S.
“Well you know, if it’s severe clear there’s really nothing wrong with that. Some Tracons are not really happy if you do it. But they’ll usually help you out with it. But again the real issue there – is it severe clear? There are a lot of dead pilots that took off in marginal conditions trying to avoid a void time or avoiding that 15-minute wait for the Citation to come in, figuring well, we’ll pick our clearance up in the air.
Take me at Columbia County. I’m departing off to the west on Victor 270. I’ve got some mountains out there. If those Catskills are obscured and I’m trying to be out there and get that clearance, I can’t climb yet. And all of a sudden once I’ve got the clearance now I try to climb. But I’m already too close to the hills; the next thing I’m a dead pilot.
So yes, you can pick the clearance up in the air, but if it isn’t severe clear, I really recommend that you don’t do it.”