I think one of the bigest factors can be the lenses, especially on dSLR's... as to why the dSLR seems to be more problimatic with sharpness over a P&S I can only assume that with the, usualy, larger sensor it is more able to resolve any minor softness of the lense.
(note, all the below are based on raw with 0 additional in camera, or conversion, sharpening)
My old G2, when the auto focus didnt pull on a noisy background, always produced quite sharp photos of the subject.
My 300D is somewhat softer in its output, or so I thought. I borrowed a good prime lense and did some experiments testing different apature settings and found that every setting was IMO better than the sweet [sharpest] spot on my 15-55 kit lense. None of the tests involved resolution charts, just day to day objects.
After a good lense, I would say camera shake is the next bigest "softner" of the whole shot... with a longish lense the slightest movement of the camera can have a masive movement of the subject of focus in the film plain.
Motion blur can also make sujects look very blured, it is supprising just how far someone can move in the tipical 1/60'th that a lot of cameras decide is the acceptable default speed in auto(ish) modes.
Photographing a rock venue using 1600ISO and setting the camera in full manual to get enough exposure I had to use arround 1/60 (small venues so not the large venue megga watt lighting systems, lol) For some reason the shots all seemed to focus on the black mike stands while the singers seemed very blured... I initially thought it was a camera AF problem, but it turned out that it was the singers movement (heavy metal) causing the blur, when they sang a couple of slower ballard shots every one seemed far sharper on the subject and still a sharp mike stand in each shot.
As to how much sharpness is good, its very subjective... some shots look good pin sharp, others gain from being soft focused. One of my favorite shots was a cock up, the camera focused on the flash screen behind the subject leaving the subject and the bed lovely and soft focused, the flash screen in focus totaly vanished when it was blown out in the highlights.
Portrates can often look nicer, or kinder to the subject, if they are a little soft.
Jon
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