I have been used various cameras since I started doing photography seriously. First, I used DSLR, then I found that rangefinder is the most suitable camera system for me.
The first camera system was Canon D30 with a Canon 50mm f/1.4, and Canon 28mm f/1.8. I had enjoyed using this system for years. When I decided to do photography as creative act, I thought that seven years old camera was not good enough so I bought Canon 50D. I used 50D for about two months but did not like quality of image file, so I changed it to Canon 5D. 5D certainly produces good images, but when I tried rangefinder Leica Ms, I was so impressed about viewfinder, manual focusing, size, weight and build quality. I bought Leica M8 and since then, Leica digital Ms have become my main camera system.
Other cameras I use are Canon 5D mk2 with Canon 50mm f/1.4, and Tamron 28-75mm f/2.8, and recently obtained first micro 4/3 system, Panasonic LUMIX GM1 with Panasonic 12-35mm f/2.8, Panasonic 25mm f/1.4, and Panasonic 20mm f/1.7 along with kit lens of Panasonic 12-32mm f/3.5-5.6.
For flash photography on streets, I am using radio transmitter and receiver of Yongnuo RF-602. The price is so reasonable that I have many of them for convenience and backup. My main flash was Canon 580EX II before and now I also use Yongnuo YN 560 III flash. Yongnuo flash has builtin receiver and again price is reasonable so I am satisfied with the product. I broke flash couple of times on streets and will do in the future as well. All incidents were all my fault; flash on stands felt down with wind. The repair cost of 580EXII is about $200. The price of YONGNUO flash is $75. I do not need TTL function so Yongnuo flash is good enough for my flash photography on streets. I use them on Manfrotto 1051 BAC stand with 026 adapter and Manfrotto 682B Self Standing Monopod.
For bags, I use two Ameribags DNA83914 for camera and other stuff. I like its ergonomic shape and can easily carry two bags at the same time when I need. Bag for stands, I use Hakuba PSTC100 Tripod Carrying Case which is durable, lightweight, and easy to carry.
Thinking about choosing camera and lens, I always try to use them for at least a couple of weeks and experience them how they work in my photography. Camera system is a tool to take photographs and tell something through own vision. Trying new tools is knowing about their capability and limitations.
In order to use tools well, we need to do practice just like learning musical instruments, or sports. This is the most challenging and fun part of photography.