The engine is now completely winterized! As it turns out I was priming the engine exactly correctly, and the problems with getting the engine restarted after the fuel filter change were related to the new rubber o-rings that were installed. It would have helped if I knew that I was priming the engine correctly. I had never primed the diesel myself, and spent a long time convinced that the filter change had been successful and that I couldn't prime the engine. Now it is finally taken care of though, so we can move on to some more productive projects!
The next project is to fix the voids in the hull seam on the bottom of the keel. I ordered some epoxy putty, and epoxy resin and it arrived last week, so with a little bit of warm weather this week we should at least get the voids ground out and cleaned, as well as start taking gear off the boat to inventory what we currently have.