Yeah, the breaking changes that accumulate over the years is the main nagging thing I have to keep up with. Since I use my apps myself, and tend to use beta iOS releases, I can usually catch these pretty early, but not always.

As an aside, I find it a lot easier to bring in consulting gigs if I aggressively open source tools that I make, and then promote those OSS projects. I find it more pleasant to tell people about free tools than to just promote myself alone, but they end up feeding into each other. Just my two cents.