Ok that's too much for me to look at all at once, but I promise I'll get back to them. Answering your specific question in the PS before I comment in general on the first three or four.
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PS: Do these look sharp enough for you guys? So many portraits I see on studio's web sites are so extremely sharp I don't know if it has to do with their lens (I have a 28-90mm 5.6 kit lens ) or post processing techniques - anyone have a clue? I actually had to sharpen every one of these!
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Sharp enough?
Yes. You did a good job focusing and giving nice bokeh for a casual style portrait.
Anyone have a clue?
Yes! You will ALWAYS have to sharpen to some extent. The only difference is a preference on how much, and whether you do it by hand or in the camera. If you shoot jpeg, every good DSLR will have some degree of control over how much the camera automatically sharpens jpegs, with some cameras giving more than others. If you shoot raw, no sharpening is done and it must be done in post processing, either manually or through automatic defaults in the conversion program. HOW sharp is a combination of personal style, lens choice, and quality of focus.
Ok, on to specific pictures. Keep in mind I'm going off my gut level feeling, I'm more used to working with semi-pro models than doing normal portraits, so I'm having to guess how I'd react, if I was a customer.
1: Cardinal sin #1 as well: Subject facing into too bright of a light, so he's squinting! Wrinkled brow! Possible solutions: Turn him more using a reflector and lens hood for glare, turn him and use a fill flash, use bright shade instead
Good composition, good color, good depth of field. Overall, I'd like it if it was me, but I wouldn't buy it because of the squinting.
Possible PP improvement: Search for the eyepop tutorial here and bring them out a bit.
2: (Street, side leaning) Squinting again! This time the squinting isn't as bad because the pose is very James Dean so the squinting works with it. As a casual faux candid portrait, I like it. What I DON'T like is the cars in the background, so a possible improvement is either a prop car (if you know someone with a fancy car you can use to cover everyone else's ugly cars) or finding an emptier street, or of course fun with photoshop magic to hide them.
3: (Looks like alley, head on, buildings on top right) Like the picture, don't like the crop. Half a hand is generally considered to be awkward. However, it'd probably work as an 8x10. Again, try popping the eyes. The sun behind him makes a great fill light. Possible post work: consider auto bracketing and combining exposures to bring the sky up a bit.
4: (Leaning on barn door) LOVE it. Love his attitude, love the modern rustic, love the colors. Pop the eyes a hair and you're done. Frame it, hang it in the hallway. Great soft shadows, great rim lighting, vivid colors, slightly off center subject, good depth, flattering angle.
5. (Peering in barn door) Would love it with a reflector for more fill light. He's a tad dark compared to the background so he gets a bit lost.