Actually not that dumb:

most boats do take on a little water but obviously the goal is for them to be bone dry at the end of the day. A quart or two is not a serious amount and you will find that the rougher the weather, the more water intrusion you will get. If it were my boat, I would try and figure out where it was coming from to make sure that it is not a precurser to a more serious problem.

There is a bit of a debate regarding life jacket over or under trap harness. They are designed to go under your life jacket but I do know of some people that put them over top so that they will be easier to get out of. I prefer comfort and put the life vest over the harness. David with Team Weathermark remarked to me a couple of weeks ago that he puts the straps of his trapeze harness through the arm holes in his life vest - it keeps the vest from riding up and hitting his chin.