Not sure about your weather in MD, but in the Chicago area, we get strong winds and sometimes lot of snow. I made a cover the first year I owned my O'Day 322. It was UGLY, and a pain in the @ss to install....took 2 days of cutting wood for the frame and to secure the tarp at the toe rail. It did however keep the snow and ice out of the cockpit and off the decks.
For this winter layup, I bought a new custom-mad cover for her from The Canvas Store. Saw them at Strictly Sail Chicago last winter. The new cover comes in 3 sections, and was custom made for my boat. The new cover went on easily, and I was done in a couple,of hours.
I never covered my Hunter 280 in the 5 years I owned her (and always took off the dodger). I always felt that the snow and ice and freeze and thaw cycles were not good for her, so made the investment in the winter cover for the O'Day 322.
I do see some boats in my marina with the Dodgers and bimini's in place over the winter, but I cannot imagine that the extra UV exposure, strong winds and potentially heavy snow loads would be good for the canvas, eisenglass, and frames.
Greg