My roommate, Dave. Taken around 4 o'clock, in the shade.

I need help with portrait shots. I can shoot landscapes just fine, but I SUCK at shooting people.

Are there any tips that anyone can give me, in specifics to my camera (a 350D/Rebel XT w/ stock EF-S lens), that will aid me in a few things?

1) I'm looking to get the sharpness around the "outside" of a person, and their features, while maintaining the softness of the skin and such when I shoot indoors. I understand lighting, and can work around having a kit (we've got some flourescents, halogens, tungstens, gels for them, etc). Most of the time, I get good lighting, but everything is too soft, and looks almost blurred, even after I sharpen it in post-processing. I've tried almost everything I know how to do -- always shooting with a tripod, shooting in different modes, aperature/ISO adjusting, bouncing the flash, no flash but certain lights.. i'm out of ideas and it's driving me up the wall.

2) Outside, what are some general guidelines to follow? The shot above was taken in the shade on a sunny day. The lighter shots that weren't in the shade aren't so bad, but they're still blinded.. and when I adjust my aperature/iso appropriately, I still can't get the shot to come out well. Any tips?