Just re-registered in the forum after about a 3 year absence.....had to respond to this thread....
Here's my thoughts....
I started in October 2005. I went out and bought a TON of equipment - a lot of it I didn't need. I submitted to a lot of microstock agencies and I dabbled into the world of traditional stock. I made some money, I lost some money. In April 2008, my step-father passed away and I sold about $30,000 US in equipment for about $12,000 so I could help my Mom pay the bills. She needed the money quick and it was all I could do to help.
At that time, I had three bodies - a 30D, a 40D, a 1Ds MK II, Quantum Q-Flash, three 580-EX, lots of L glass, etc., etc., etc.
About a month ago, I started uploading old images again and I started shooting again. Photography is something I HAVE to do - it's a great outlet for me and it's a calling.
Here's what I've learned from my experience....
1) Microstock is not the only market for images - find your market. If you like to shoot events, find an organization near you that will give you access to shoot, then market prints and small sized electronic images (so they can post them on Facebook) to the participants. Image quality doesn't have to be exceptional. If the events are newsworthy, then find an agency that will market those same images as editorial. If you like to shoot wildlife, then spend a year shooting, put together a 200 image portfolio, and apply to Animals! Animals! or any other stock library that specializes in wildlife.
If you want to shoot architecture, then get a Sigma 8-16 lens and get friendly with your local real estate agents. They'll only pay you $50 - $75 for their cheaper listings but you can market the images on their "staged listings" as stock after they pay you to take the pictures. If you have a friend in real estate, he or she may even allow you access to homes so you can build your portfolio and get practice.
2) Equipment can be expensive, but it can also be relatively cheap. One thing I learned the first time around is I prefer fast glass - I had to buy the slow glass first to learn this though. The first time, I had a 17-40, a 24-105, a 100-400, a 70-200, a 16-35, a 100mm macro, etc., etc. Consider renting equipment before you buy to learn what you like. One of my favorite lenses is a first generation 50mm f/1.8 that I picked up on eBay - Adorama had the newer version in their used area last week for $65.
I was shooting a rodeo at an indoor arena over the weekend. The lighting sucked. A friend was with me and we had all access press passes. The friend was cussing up a storm on Saturday because the lighting was so bad, we couldn't get a good shot of the running horses. She was shooting with a 4 year old Canon Rebel and she was blaming the camera because she wants a 7D and I was shooting with a 7D. When I told her to change focus settings from AI Servo to One Shot, and then I handed her the faster lens (canon 50mm f/1.8 ) she started seeing better results. It's not the price of the euipment - it's learning how to use it for the situation at hand.
3) You don't need a carbon fiber tripod or a 430ex for your camera. You can get a cheap (in price) set of Bogen 3001 or 3021 tripod legs used for about $50 and a good tripod head for about the same. You don't need to spend $200 on a tripod. Heck, you can get an aluminum tripod from Target or Walmart for about $40 with head to get you started.
Instead of a 430ex, why not start with a Vivitar 285HV? Amazon sells them for $90 and it's a great flash - recommended by photography schools everywhere. It's manual (doesn't have TTL) but once you learn how to use flash, you can upgrade to a 430ex and cables or add a pocket wizard so that you can use the Vivitar for a second flash (fired remotely). With a single flash unit - you can shoot outdoor portraits in full sunlight without a problem.
You can get a Vivitar 285HV for $90, a "strobist" light stand and umbrella kit for $42, and a required PC cord to your camera for about $8 and you've got a terrific flash setup for $140.
http://www.amazon.com/gp/product/B00004TVSPhttp://www.amazon.com/gp/product/B004HR0M4QThat's $260 less than your estimate for a "stupid flash" - for that amount, you could have a two flash setup.
There are a lot of folks that started with nothing - and coming back after a few years, I think the comments about "it was easier in 2005" are unwarranted - mostly because back in 2005 people were saying the same thing about folks like Webking or LisaFX or anyone else who put their best foot forward and busted their butt to develop their skills and learn the business - learn the market.
Some things to keep in mind......
AndresR started with a digital rebel and Photoshop
PhotoEuphoria started by saving money for a cheap camera and shooting people using her closet as a studio
Heck, there used to be a guy on this forum THESUPE187 or something similar that started with illustrations and learned as he went along.
The bottom line is you need to learn the craft by doing it. Join a local camera club and go out on their outings and learn from seminars at the club. Nobody here can tell you how to be successful because everyone's success is simply based on hard work and a passion to do this.
P.S. - you also need to ignore a lot of what you read on forums. Everything from the folks at the finance sites like Rich Dad or Frugal Dad or whatever touting you can get rich quick by selling photos to the people on photography forums whining about this or that - get out and shoot, learn to use your camera, and find what works best for YOU. The only doors that are going to open for you in this business are the doors that you take the time to open - don't be afraid to knock on those doors.
