I really struggled with this returning from Oshkosh. I got a late start and was a few gallons short of full. I could make the flight non-stop to the east only if I overflew the lake or cut the corner over Chicago. While I could fly VFR down to Chicago, the rest of the flight would be at night, high and with occassional clouds so IFR was required.
I really didn't know the procedure for a VFR/IFR composite plan - that's what I recall them being called. Using Foreflight I attempted to file an IFR plan starting just past Chicago at CGR direct to Delaware. Foreflight required a departure airport so I added OSH and a comment that I would be VFR to CGR at 11.5, over the Class B. I got back an expected routing that circumnavigated Chicago by a wide margin, just as the clearance I rec'd in to Osh a few days ago.
So I departed Oshkosh, climbed to 11.5 and found a FSS freq to file another IFR plan from CGR to destination. Once that was done, I contacted the closest approach to open the plan while over the Class B. They immediately picked it up, cleared me direct and gave me vectors for traffic. That all worked quite well.
Flying in and out of White Plains IFR, the clearance in from the south always goes low and around to the west. However on the way out it's always right over JFK at or above 6k as I recall, consistent with the post getting VFR transitions at 6500. Does anyone get that going west to east?
Doing a NJ to Montauk roundtrip, I file IFR and was being sent north to Fishkill or something . I tried to negotiate with the controller for something less onerous but finally said cancel IFR and he immediately cleared me for a direct transition to Montauk. Got the same on the way back. VFR was the key to going thru the Class B that day. Watching NYC light up at dusk is quite a sight.
Transitioning thru Charlotte IFR, they bring you right over the airport but never higher than 6k. I usually have to descend to transition straight thru. Wish that kind of thing was published somewhere... is it?