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As an artist, I feel the greatest connection to a painting when I have had the chance to meet the subject and personally take their photographs.  Often after taking photographs, I do a color study which is a small unfinished painting that notes various colors that I see in an individuals skin, hair and clothing.  While photographs offer a lot of valuable information, there is a lot that needs to be observed from life.  However, there are circumstances in which other people's photographs are the only thing you have to work from as in the case of the posthumous portrait.  In that case, I find it helpful to look through many photos and videos if the family is willing to share.  It helps in getting a more accurate overall picture of the person.  

Sometimes a photograph is just a nice photograph!  People often have photographs that have great sentimental feelings attached to them and they would like to have them turned into a drawing or painting.  Experience has taught me that the quality of these photos is directly correlated to the outcome of the portrait.  I've been given photographs where the part of the person's head has been cropped out or the sun has bleached out the features of the face.  These photos make a really nice photo, filled with memories but it isn't something I would want to take further.

Too much cheese!  We have been conditioned to smile for the camera...say "cheese" and show all of your pearly whites!  These poses make for fun photos but aren't necessarily good references for paintings.  I often like to capture a more thought provoking pose for painting references.   However, if a client prefers a pose with a large smile, I am all for it but usually the poses are more subdued.

I'm not photoshop!  In the past, I have been asked to use a head from one photo and a body from another or fill in information that is missing.  These sort of requests can be tricky and in most cases, I wouldn't want to use these photos as reference for a painting.  

These are stylistic choices that I personally have made with regards to my work but there are artists that are comfortable with these types of requests.   Painting the portrait may mean something different to each artists and when commissioning a painting, it is important for the client and artist to be aligned on the final outcome.