Clearance Roulette (cont'd)

The ATC computer seems to have trouble getting N631S and me a workable clearance for our Monday morning trips from DC to Connecticut. As usual, there's a back-story to the tale.

Early on, I would file something like:
POLLA V312 GOLDA V268 ENO V16 JFK V229 PUGGS at 7,000 feet.

I learned very quickly that I'd be required to descend to 5,000 feet approaching ENO if I wanted that routing. Period. And that was annoying because I'd just used all the AvGas needed to get up to 7,000 where the air was clear and the tailwind stronger.

But a helpful Dover Approach controller told me that if I would accept direct LEEAH V1 JFK etc. I could stay at 7,000. So I started to file for this route:
POLLA V312 GOLDA V268 LEEAH V1 JFK V229 PUGGS

That's the red line on the graphic above. The V16 route includes the segment shown in green from ENO past VCN and up to CYN.

The route from ENO via LEEAH and V1 works well for me, but the ATC computer seems to have a bit of trouble spitting it out. When I file, and then check the FlightAware.com site to see what routing I should expect, it shows this odd version:
POLLA V312 GOLDA V268 ENO V268 LEEAH V1 JFK V229 PUGGS.

What is the point of inserting ENO into the middle of V268? (ENO is the Smyrna VOR near Dover AFB.) I got a hint this morning when I telephoned Mount Vernon Flight Data to pick up the clearance. The controller said, "Can you hold on for a minute? You have a "pref" route out of my airspace and a "pref" route into New York and I have to get them to mesh." A few minutes later he came back with this:
POLLA V312 GOLDA V268 ENO V16 JFK thence As Filed.

Well, that's not what I want! That's going to make Dover Approach issue me a descent to 5,000. But I accepted the clearance with the intent to try and work something out en route.

As soon as Potomac Approach told me to contact Dover I switched frequencies and said, "Good morning Dover Approach, Skylane 631 Sierra level at 7,000 with a request."

This got me, "Skylane 631 Sierra, Dover Approach. Dover altimeter 29.64, say request."

Me: "Skylane 31 Sierra is cleared after Smyrna, Victor 16 to JFK. Requesting after Smyrna, Victor 268 to LEEAH then Victor 1 to JFK and maintain 7,000."

Dover: "I have your request."

About three minutes later, the Dover Approach controller was back with a routing change. He cleared me present position to ENO, thence V268 LEEAH V1 JFK, rest of route unchanged. Perfect.
But it seems like a lot of effort to do something that ought to be simple.

Well, that's IFR flying in the Northeast.

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Since I make these trips every week, I guess some of the controllers are getting used to me. I had the following exchange upon checking in with Atlantic City Approach:

Me: "Good morning, Atlantic City Approach, Skylane 631 Sierra, level, 7,000."

AC Approach: "Skylane 631 Sierra, it must be Monday. Good morning, Atlantic City altimeter 29.62."

Me: "29.62 for 631 Sierra and yes, it is indeed Monday."