JFrancho, I may have misread your post, but I think the mentality that he is safer buying new because he is up north is a wrong one to take. Regardless of where you live, the boat is going to take a big hit the first year of ownership. The price he will pay for new will be a few grand higher than what someone can get the same new boat for next spring and will be many thousands higher than what he could get just a few year old boat for. In looking at the boats for sale site, a boat just 3-4 years old can save you a minimum of $10-$15K on some models. The largest hit on value occurs in the first few years.
As far as the OP, just being out of college, one shouldn't be taking on debt of this type when one could get something very similar for many thousands less. I understand the "want" aspect as I was that age not so long ago. I've made my mistakes and now realize that toys like this are best bought used where someone else took the plunge and also took the hit on the de-valuation. The economy is in the crapper in many areas still and people are willing to part with some items for about what they might owe on it. In some cases, this can mean a very sweet deal.
I would also consider what someone said above about running costs. I am also looking at purchasing, though used. The difference in fuel costs alone can be enormous between engines. For this reason, I know that it is doubtful that I would purchase any boat with a 250hp engine.