Some of my neighbors have added skylights and a couple have had a lot of problems with leaks. Are skylights a good idea or would I just be making my life more complicated?

Top quality skylights installed by a conscientious pro almost never leak. Unfortunately, many homeowners get a bargain basement "special" skylight on sale at the local home center store. They have problems getting a real roofer to install it because reputable roofers don't want to have anything to do with one of these budget skylights. The homeowner resorts to having a handyman install the skylight, and so begins a litany of leaks and problems.