actually, for those composites, the lighting hardly changes, so the only thing to watch out for is to look for people isolated (instead of walking in groups) so they can be blended in better with other people
i wonder how he set some of these up. i guess a few must have had the camera posted up by a lamp post or fire hydrant or in the shade right next to a building, but for some i know you can't just set up a tripod in the middle of a busy sidewalk. he had to have some kind of fairly tall rig that he put his camera on... maybe a hand truck with some boxes and and the camera hidden inside a box. or a big guitar case that can stand up with a hole cut out for the camera. on top of that, he's definitely got some nice composition goin on, so i guess he probably used some kind of video out and a remote shutter trigger.
pretty damn original... i gotta try this out