This particular image was the first that caught my eye and although comments have already been made I figured I'd add my thoughts too.
Since I'm not voting on this as the challenge is over, most of my commentary will not be about the challenge requirements - though I think it meets the challenge just fine.
Now that said, I'll get into some of the technicals (mind you I'm no expert so keep that grain of salt handy). Firstly, I think the overwhelming issue I notice before all else is the head position. As mentioned it looks TERRIBLY uncomfortable. While it may not have been, the impression actually does leave a residue on how I view the image, and does so negatively. I think its the combination of her head being turned to a rather extreme-looking degree and her head then being tilted upwards as well and the smile looking just a bit forced as a result.
I would suggest having her lower her chin so that it is parallel to her shoulder or even slightly lower so its pointing down towards the shoulder region - this will need to be adjusted depending on if she has looser skin around her neck as you don't want to show more wrinkles or double-chin if that's an issue (from this view it doesn't look as though it would be, but you never know!). I would also suggest bringing her head in towards her center more - I think a good starting point would be to have her head in line with the outer edge of either the left or right breast. This should give a nice angle to the head and yet not be quite as extreme as is shown here, depending on what side you/she considers her best side would determine which direction to turn the head.
Next is the focus, which has been mentioned as well, I don't think the focus is terrible by any means, there is a sort of blanket of softness but its not blurry. With portraits I like to see very sharp focus on the face, and most especially the eyes. If the eyes are sharp then a softer focus radiating outwards from there is acceptable (if handled correctly), though if you can manage a sharpness throughout the entire face, all the better IMO.
The lighting is a bit flat, though I don't know if some of that is due to the transition to B&W or not. I think two lights, one shining straight on and then another coming in from about a 45 degree angle to clear out any stark shadows the first light created would be worth trying. If you have a reflector that you can shine the 45 degree angle light into and bounce onto her face that may help and if you have a diffuser (home made ones can be created from tissue paper or even white trash bags) that would help control the main light too. This might address some of the bright reflections on the cheek and nose. Not sure if some makeup powder would help that too or not.
Compositionally, I think filling the frame with her face was a good choice, if the angle wasn't so extreme then I'd say the composition was nearly perfect - Cropping just a bit from the bottom so the smidge of shirt was gone would clean up that area some and being aware of the environment is key as the bands of black& grey up at the top push the image balance way too the right and looks somewhat out of place.
Not having seen the original of this, I cannot say whether B&W was the best choice. There are a lot of midtones here which end up translating into greys or softer blacks & whites which don't give you that nice crispness you can see in other B&W images. This abundance of grey tones also tends to have the effect of making the image look dull or sort of washed out.
The headband does make for a really nice line and a definite contrast that is pleasing to the eye. I wish there were more sharp contrasts like this, it would really add drama to the image. The other thing about B&W is it washes out the color of the eyes, sometimes if the eyes are really really light or really really dark this can work in the images favor, but if not, then a large point of interest can be lost.
Sooo, after all that I'd say, the key points for this particular image are: focus, position of your model's body parts and your model in the environment. Even with the the current lighting and the flatter grey tones shown, an adjustment in those three areas I think would improve the image greatly.
Hopefully, there is something of use for you in all that babbling, I'm no portraiture expert but I do know what I like to see as a viewer! By the by, I think the voters were overly harsh with this image. I don't see it as a below 4 image.
Back to comment: Sorry to say but this image doesn't really convey Simple Pleasures to me. She doesn't really look all that happy and there is no indication of what is bringing her pleasure. On the technical side, it appears that the image is out of focus. This could be a result of not sharpening the image after resizing or from camera shake (Not using a tripod in low light conditions).
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