Question 1 - Is pocket camera right for me?
Maybe. For $200, there are a lot of cameras on the market that takes great pictures, and iPhone 4S also takes decent photos with some practice.
The real question on choosing a pocket camera is about "DO YOU WANT TO CARRY TWO of same thing"? I would carry iPhone and a pocket camera if the POCKET CAMERA is really easy to use, and it has something to offer.
Things I found useful with POCKET camera
1. Wide angle lens
2. Fast lens (low f/stops)
3. Good grips
4. Optical view finder (old school)
Most of pocket cameras all have some range of manual control, video recording etc. But it's about pocket camera, not do it all device.
The next serious question would be, are you willing to turn over- $400 for a pocket camera?
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Question 2 - DSLR? Am I ok to be seen with a large camera hanging on my neck, all the time?
In the 70s, and 80s, people wear cameras on their necks. Nowadays, people pull out cellphone to take pictures. Once you decided that you want to take good pictures and don't might being like a Japanese tourist, the weight of bulky DSLR, then how far would you go with your camera gear?
Some will carry a camera bag with many lenses and a tripod - at all the time. Is it too much for a vacation trip? Most people would say yes. I would take a DSLR with 1 or two lens for the trip, or wedding events.
Here are a few things I found essential to a DSLR setup.
1. DSLR camera body is all good. The lens does the magic more so than the camera body.
2. Ultra wide wide angle lens 15/16mm (35mm lens equivalent) - It is not practical for most people, but it is great for landscaping.
3. An all purpose lens 27/300mm (35mm lens equivalent) - It is heavy and expensive, but it is great for everything.
4. Light weight,very fast f/1.8; f/1.4 fixed lens 50mm (35mm lens equivalent). It is great for everything, but you need to move with your feet a lot.
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Question 3 - How much should I spent on buying new gear?
This is an easy question to answer, but with a twist. If you're really/seriously into digital photography, then be prepared to upgrade your equipment every 2-3 years, even though it still works.
How much should you spend on new gear? You know you paid too much when you need to make an effort to notice the obvious differences (convenient, quality, functions etc), and the equipment yields forgettable conveniences and providing the functions you rarely usede.
Maybe iPhone is the only device you need.
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Question 4 - What do I have? And what do I want to buy/upgrade?
Wish list -
Two digital SLR bodies,
Nikon D5100 (all purpose lens DX 18-200mm, one with all-purpose lens)
Nikon D90/D700 (special DX 11-16, fast lens, one with -ultra wide angle lens)
External pop/attached flash unit (Nikon SB600/SB400)
One Normal Low light/fast lens (DX 50mm, DX35mm f/1.8)
One Tele-photo Low light/fast lens
Pocket Camera - Sony Cyber-shot DSC-WX9
25mm lens f/2.8 (still photo); low price ($150-$160)
size of cell phone,
http://www.digital-photography-school.com/13-lessons-to-teach-your-child-about-digital-photography
