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Dealing with portrait in natural lighting

pic looks fine. its plenty sharp. i think your being to hard on your self. plus setting for portraits with natural light vary greatly given your conditions. so there is no easy answer.
 
Another quick question

How far does one usually shoot the subject? Lets say 50mm, how far would you place your camera within the subject?

what is the minimum focusing distance specified for your lens?
 
Another quick question

How far does one usually shoot the subject? Lets say 50mm, how far would you place your camera within the subject?
at 50mm the field of view is fixed, so distance depends strictly on how much of the person you want in the picture, i.e., kind of portrait (headshot, waist-up, environmental etc: I do not know english terms for all kinds). Nothing you can decide independently from that. It depends also on sensor you have: APS-C (smaller field of view) or FF.
On the other side, you may decide which focal length to use to obtain the best effect (i.e., reduce perspective distortions). An headshot typically calls for longer focal lengths.
 
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I did a little work on your photo. Using ACR 6, I 'Recovered' some of the blown white shirt. I decreased the Saturation a bit, but increased the 'Vibrance' a bit. I added a bit of 'Clarity'.
In Photoshop CS5 I straightened the photo using the vertical lines of the windows. You can see how much your camera was tilted by the long white triabgles on all 4 sides. I selected their eyes and increased the exposure 0.75 stops. I dodged his teeth to make them whiter, and I cloned the catchlight in his left eye and applied to his right eye. Lastly I increased the mid-tone contrast a bit.

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