I have a similar story to most every photographer. Took a film class in high school and fell in love with photography. Right out of the gate, I bought a Pentax K-1000 kit with a 50/1.4 for about $300.00. Shortly after that, I decided that an auto focus camera with a wide zoom range would take my photography to the next level: Minolta Maxxum HTsi + 28-200/3.4-5.6 for $1000.00. Then I needed a longer lens: 200-400/5.6 $650.00. Then, you know what, everyone is experimenting with wide-angle photography. So, I added a 17-35/4, $500.00. Now, I am started to have a pretty good kit, I have almost $2400 bucks invested (plus, probably several hundred in accessories, bags, lens cap holders, etc.). And, gee, if I want to continue to grow, I need a flash or 2. So, lest add 2 flashguns: $600.00. And remember, this is all film equipment, so I am paying for film processing, etc., etc.
Now, fast-forward a bit. I am pretty happy with my kit, but as I get more serious about it, a camera body with OTF (off the film metering) and some other must have things come along, so I add a Minolta Maxxum 5 to my line up, $800.00. Now, things are starting to open up for me, I am starting to work with my cameras (actual paying work), and I am really getting excited. Digital cameras are becoming more mainstream, with 6 megapixel slrs hovering around 3k. Rumors are flying that Minolta will release a pro~semi-pro body soon to compete with the d100 (Nikon) and the d60 (canon). I have been buying pro lenses for my Maxxum 5, so I have added about $5k worth of lenses and flashes etc. bringing my total investment to about $8800.00. Then Minolta finally releases the Maxxum 5d, I purchased one the first day that it was available. I spent about $4000.00 on it after the batteries, chargers, memory cards, etc. Whew! I am now vested in Minolta for almost $13,000 (read: THIRTEEN THOUSAND DOLLARS!) So, by this point I am impatiently waiting for my 6 megapixel dslr, I get it in the mail, and with in a week of that Minolta folds and merges with Konica and sells all of their photography related divisions to Sony. I was about ready to cry. I now have THIRTEEN THOUSAND DOLLARS! worth of gear, no support for repairs, a completely dead system. There is not really any resale value for the camera system because it is a dead system….
At this point, there is not a whole lot I could do. I start evaluating other cameras; the canon system looks best to me, so I buy a rebel (it was cheap). then I add a few pro series lenses. And I added a used d60 a few ef-s lenses (for crop sensors only).
Now here is where I am getting to the point from all this rambling. I am working much more buy this point. I am still using the Minolta system, supplemented by the canons, working with 2 different systems is kind of a pain in the @$$, so the time to consolidate into one system is overdue. I ended up purchasing a canon 5d a few flashes and a handful of lenses, all in all about $10,000. Now here is the interesting thing, by this point, I am pretty versed in photography; I bought the best system that I could afford (I had stopped trying to save money by purchasing lesser equipment). I bought the 5d in 2005. It is now 2013 and I am still using the 5d professionally. I look back in hindsight, and think to myself, if I had put a little more planning a thought in to the purchases that I made I could have saved thousands of dollars. The 5d cost more, sure, but in the long run, it has proven far more durable than say a rebel, and even by today’s standards the 5d is capable of amazing image making. Early on, rather than looking at the whole picture, I was focused on incremental upgrades, I needed to have OTF metering, or what ever the rage was at the time… rather than looking for a camera that would grow with me and would allow me to make virtually any image that I wanted or needed.
A friend of mine currently has a rebel series canon. He is thinking it is time for an upgrade and is looking at a 7d, but that is close to maxing out his budget. He is thinking what he really wants is a 5dmkiii. I did the same thing he is planning, which is buy a rebel, then a 7d then a 5dmkiii, but if he just skipped the 7d and held out for a time to get the mike, he would be in a much better place. True, hindsight is 20/20, but I think that I could have come out about $15,000 cheaper if I would have put more planning into my purchases rather than focusing on inexpensive (relatively) incremental upgrades. So, my advice to you: Look at what your intentions are with photography. By the *RIGHT* gear ONE TIME, rather than incremental upgrades over and over.