J Mac,
I live in the Boston area and got a quote of $195 for winterizing the motor and 12/ft for shrink wrap... so a bit over 400 for both.
I decided to do it all myself instead. Well, I didn't shrink wrap but bought a half-decent decent cover with good reviews and on sale for pretty cheap. For the price, if it only lasts one winter then I break even or better. If it last a few years (which I expect it will) then I will be way ahead. I also just picked up some PVC last night and plan to build a frame under the cover this week so that the snow hopefully slides off instead of sitting on it. My boat will be stored right next to my house so I figure I will be watching it anyway and keeping it clear of snow buildup throughout the winter.
As far as the winterizing of the motor goes, that was really easy and this is my first boat. I just bought some OMC fogging oil and followed the instructions. The shrader valve on top of the motor makes it really very very easy to fog my Evinrude and my understanding is that most OMCs have this valve. Changing the lower unit oil is very simple also.
By the way, I don't have an Evinrude dealer that close to me so I ordered everything from shop.evinrude.com and it shipped from the nearest dealer and arrived in a few days.