Do I want to be in a position where photography is my main source of income? I'm concerned I'd soon lose a lot of the enjoyment if photography became work and I was dependent on it to pay the bills. Then again, if someone was to pay me lots of money and fly me around the world to exotic locations I'm sure I'd change my mind.
I also wonder how many people think that, because they take good pictures, they can make it as a professional photographer - and fail. Many will consider photographic talent to be all that is required, but we're talking about a business and lots of businesses with good products fail because those involved simply don't have a clue about how to develop and run the business.
It's definitely a much harder market now. Digital SLRs are so common and recent consumer kit will easily equal or surpass the image standards of professional level gear from a few years ago. It's certainly not uncommon for wedding guests to have "better" gear than the pro shooting the wedding - not that the gear creates the image. While the pro might not have the latest camera body, the pro should have a spares for the critical bits of kit (camera body & flash) and I'd expect a serious pro to be using better than the consumer range lenses. Decent kit is now generally affordable and that makes it easy for a lot of people to offer "professional photographic services" for ludicrously low prices as an extension of their hobby. Sadly this will suit a large part of the market who are unable to see beyond the cheap price. Of course, "you get what you pay for" and that's probably not much beyond someone turning up to take the pictures and burning straight from the camera JPEGs onto a CD.
Maybe it's just experience (I'll avoid using "maturity" because that makes it sound like I've grown up), but I really value my time - the cheap, low quality and high volume space just doesn't offer the work/life balance I need. Finding the entry into the high-end market and developing that to be a steady and reliable source of income is the challenge.