If you are on a mooring you will not be able to check on the boat for roughly a month in winter when the creeks that are shallow enough for moorings are frozen. Also, mooring for the winter can be pretty risky since holding on the Chesapeake is not all that great and the ice flows can come through and cut most mooring
lines and simply drag off the a moored boat.
Depending on the width and draft of your tri, I may be able to let you tie up in the slipway at my home.
Jeff