Unless you're really strapped for time, there's no reason to pay the pros $1500 for shrink wrap every year. I've had good luck doing it myself. Three years ago I bought the heat gun, gloves and tape tightening tool, etc -- with the cover, tape and other consumables for that year it all came to about $750 or so. This year I bought the plastic and tape I needed for about $300. (Boat - 47 ft x 15 ft.) I use Dr. Shrink (Dr-Shrink.com - International Shrinkwrap Supplier , Wrap Anything!
I will admit that it takes a bit of practice to get it right, but if you're careful and follow instructions well you can probably manage it. It's easier if you have one or two people to help and small boats are easier than big ones. I'd be happy to share lessons learned -- send me a PM.