Speed was definitely my enemy here, plus the work environment I was in. I installed an attic fan on a fairly steep roof, so between the balancing act and trying to get tools to stop sliding down the roof, it was a lot more trouble than expected. While the project wasn't difficult, it was messy and frustrating because of the caulk gun-dispensed roofing tar getting everywhere. I'm actually pretty skilled with a caulk gun, though I can never get it to not drip caulk as you move from application site to site. Cleaning up excess caulk isn't hard, but cleaning up roof tar is painful.
Owning a home opens you up to all sorts of new skills/experiences. A lot of it is frustrating and expensive, but the learning experience and a well done completed project are character-building. You could also volunteer at a place like Habitat for Humanity and get some construction experience.