Don't know if I could actually do the "long distance" ownership thing.. I like to check the boat twice a week at least esp in winter.
For long absences I think winterizing is a good idea, more so if the boat is stored on the hard. The warming effect of the water usually deals with the few short-lived cold snaps we get up here now and then so we don't bother to winterize to that degree. But we also tend to use the boat year round too.
Don't forget to include BC in your plans.