I had a few other questions in my original post. Among others, does it make sense to put an elaborate route in a VFR flightplan?
No - the route is really there for search and rescue action should anything happen en-route. Keep this in mind when filing it and file a route which is easy to follow for the reader but is close enough to what you will fly to be useful should the worst happen.
Does it increase my chances of getting a transition through controlled airspace en-route?
No - as these units don't get a copy of the FPL. Even if they did, having the details of all possible transiters to hand on a busy summers day would be physically impossible, and so they're not really interested until you call for transit.