I also have a steep roof as well and know I have to re-shingle it. I was thinking of doing it myself if I get enough nerve up! Funny, I'm scared to get on my roof, but can fight fires (vol here in VT) on a 75' ladder, attached by a big hook to it and step on a roof in the middle of winter with a chain saw. I guess it is the whole, if I fall off my roof, I will be in pain. If I fall off the 75' ladder, I could die, so I won't be in pain. :-)
I found out it will cost roughly $2500 to re-shingle the roof if I do it, or pony up $5k to have someone else deal. I may just pay and not go on vaca!