I'm with you man, and while I'm not making money with photography (yet), I do want to comment on #1...
Quote: 1. I am scared that one day photography will begin to feel like work and I will not enjoy it like I do now.
...
I feel qualified to to comment on #1 since I've really just had a succession of this type of "passion motivated" jobs rather than any sort of career... My resume includes:
ski instructor, ski patroller, mountaineering gear salesperson / whitwater kayaking instructor, wildland firefighter, helicopter flight instructor, helicopter tour pilot, firefighting helicopter pilot (my current gig)... I called these "passion motivated" jobs 'cause I convinced someone to pay me for pursuing a passion - for doing something I would like to be doing anyway (skiing / kayaking / playing with fire / flying helicopters etc...).
My experience has been that I'm almost always happy to go to work, but there are times when because of conditions, or personalities, you can hate one of these great jobs just as much as a "normal" job... If you have a passion for photography (which obviously you do), more often than not, you'll be happy every time the shutter clicks and you know the image you're after is captured.
I'll agree with Marc (based on instinct rather than first hand knowledge) that the money is in photographing people (with obvious exceptions), but contrary to a couple of the responses so far, I would try to avoid being pigeonholed in a small niche, for your own sake. Lets say, you developed a niche shooting just graduation / prom / senior portrait type of work... you may eventually make a decent living just focusing on this one type of work, but repetition - the feeling of being stuck in a rut is where any job, "will begin to feel like work..." I say pursue that work (or whatever can be your bread and butter - weddings come to mind
), while cultivating other styles too - product shots, food photography, golf photography, etc. whatever interests you and you can do justice to, try to keep your hand in that type too, because variety is what keeps a job interesting for the long haul.
Honestly, in this market, I'd probably grip white knuckled to any job you still have, and try to get photography "work experience" in your spare time, but I don't know your situation well enough to really comment. I'm imagining that some of your web design clients may need photography too (whether they know it or now
), and you may be able to leverage some work out of your existing relationship..
A question/caution I have is in regard to your comment, "My website company has it's perks, I can release my creative side and get some play money but dealing with people/clients is starting to wear on my."... What is it about the people/clients which is wearing on you? Because I imagine it will be the same or worse when they're paying you for photography. Seriously, I think that dealing with ridiculous clients is the hardest part of every job - you want their money, but you just wish they'd go away sometimes - this continues to be true even when dropping water on wild fires - it's the people side of the job which is often the hardest (no offense to my main fire crew I work with - you guys rock!
(I don't think they read this forum, but one of 'em does own a K20D - he may lurk here... you here Justin?)).
Finally, don't get discouraged about a field just because it's already fairly saturated... you don't have to be in the job longer than everyone,you just have to be
better than a fair number of 'em
.