For me, the most important thing is that the battery last all Summer long, not go dead just when I NEED to go fishing.
Having it on a constant charger all Winter means that the battery is at 100% all the time. It doesn't tell me what the condition or remaining service life is.
I charge monthly. Before I hook it up I check the voltage. If after a month of no use its still at 95%, I know it will last the full next season. If it drops below XX%, I don't bother wasting the energy to charge it any more, but plan on replacing it the first of May. Yeah, I could probably get another year or 2 by charging during the Summer, but life is just too short to be bothered with it. Hassle elimination is the name of the game.
If the car dies and i can't go to work, so sad so sorry. But if the boat won't start on my day off its a major catastrophe.