Interesting videocast(s) from Scoble -"Photowalking with Thomas Hawk" (in four parts 1 2 3 4). Thomas Hawk is a semipro (or very enthusiastic amateur -- it is hard to pigeon hole him) San Francisco area "street" photographer with high tech connections (so he runs in the same circles as Scoble).
He has some interesting strategies and photo techniques. He uses a small group of extremely fast fixed focal lenses (from the comments it is not clear whether he even owns zoom lenses) and doesn't use flash at all. He talks about f2.8 lenses as slow! He has fully embraced the digital world -- often doing a lot of after picture taking computer manipulation of images. Seems like is the ultimate photo geek going everywhere with his camera and taking 100's of full frame RAW pictures a day.
It would be hard to emulate his technique and strategies without extreme dedication or winning the lottery though, considering he probably uses and walks around with as much as $10000 worth of equipment. Most of the rest of us have much more modest budgets.