At the moment my question is hypothetical, so there is lot's of room for
adjustment. I'm changing jobs and may decide to live aboard to cut down
on commuting. Living on the hook gives me more location flexibility;
there are not many marinas in the D.C. area that allow liveaboards.

I have a grip (or at least an initial plan) on heating and maintaining
electrical power for the boat (diesel heater like Webasto or Espar and
solar and wind power supplemented by the generator -- still cheaper than
slip fees).

Still unclear to me is getting back and forth to land in the winter. If
the distance to a dinghy dock or other landing where I can keep my car
is too great for rowing, how do I keep an engine operating through the
winter? Any specific suggestions for a commuter that minimizes how wet I
end up in the rain?

I may just be insane for contemplating this, but part of my motivation
is to avoid being tied to the dock by "extra docklines" like telephone,
cable, water, etc. I think I'll sail more often if I'm on the hook than
in a slip.

regards, dave