I have propose this idea to Bill a number of times, Phyllis K Lang over at Knightware has tried to contact Bill about putting together an interface that would allow Deep Sky Planner to work with Guide. Which already interfaces nicely with Chartes du Ciel, Redshift, Starry Night, and The Sky. Strangely Phyllis says that Bill did not respond ...
I have a number of friends that are currently using Sky Tools just for the very reason that it allows them to create a planned observing session. I for one would love an interface between Deep Sky Planner and Guide.
Just my thoughts ...
Mark S Deprest