IMHO, drilling holes in the roof is a moot point now. We have so many good products from sealing to gathering and penetration design that there is little to worry about from a product or leak perspective. I think the issue is more with your situation is your self proclaimed lack of Handy-ability. I've been on my roof regularly with my weight varying from 215 to 260 pounds and have done no damage. Actually I repaired a broken(cut actually) truss, so my roof is better off with me tramping about on it. It could be possible to minimize the amount of time you're on the roof by using a ladder. Or possibly if you have a buddy that is handy, you could assist him with the work while he spear-heads it.
