paul kgyy wrote:
I was taught that, if I needed to file an IFR flight plan in the middle
of a trip, I should contact FSS first to file and get clearance, then
contact ATC. On the other hand, I hear frequent references in
rec.aviation to pilots who just contact ATC directly. Does this depend
on how busy ATC is - i.e. near Chicago contact FSS, near Moline contact
Moline approach?

It absolutely depends on how busy ATC is. Around here (New York), if
they're not busy, you can call them up cold and and make your
request. They'll take the important info (destination, aircraft type,
etc) and give you a route. Sometimes they'll say they're too busy and
tell you to go talk to FSS like you're supposed to.

What I find works best is if things are iffy, is to get VFR flight
following first. Once they've already got you in the system, assigned
a code, radar identified, etc, if you later tell them you need to get
a clearance, they're more likely to handle you directly.

If push comes to shove, if you tell them you need a clearance NOW,
they'll get you one. But the idea is to never let things degenerate
to the point where you have to start playing trump cards.