Most people would say that doing it yourself saves you a lot of money. And in general I agree. But at what point do you stop and hire someone? We've done a lot of home repair, definitely more than average and I know my DH is handy. His family did pretty much all DIY. Unfortunately they learned the hard way that you occasionally should just pay someone to do the work around the house.
For example, our condo undertook building a backyard retaining wall. Beautiful, cheap, and relatively easy. Our share was $2k, great considering the additional value. However, we also need to repair the retaining wall holding up our parking pad. That is a much larger, more labor intensive job using special tools, not just hand. Could we have undertaken rebuilding it ourselves? Yes, but the scope of the project definitely made it worth hiring not only an contractor but engineer to certify the wall.
Another example of DIY not winning out is cleaning our gutters. One of our neighbors mentioned saving $150 it costs to clean our gutter by doing it himself. We nixed the idea when because we have a 5 story house and if he fell down, he'd die. Sure we'd have insurance, but there are some cases where it's better to hire a licensed/bonded professional who can accept the risk of falling off a roof. Besides the point that they are less likely to fall off the roof because they are an experience professional.
I guess the question is how to measure when a job even a small job is worth paying for because of risk, and a larger scope job is worth investing the time to do.