Mike...nice job on the blog. I think you are freakin nuts (in a very nice way!) and will regret the time and $$ you are gonna waste with this approach down the road...but hey..it is your road to travel. Just try not to push the limits with the baby on board.
BTW...med school is about a $250k proposition these days. If ya can't afford a sailboat in decent condition...how are you gonna do that in a few years after you've depleted your resources sailing? Suggest you take the boards while science is fresh in your head just to see whether you can qualify...it ain't gonna be easier in 4 years!
No longer posting. Reach me by PM!