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Near/far size perspective is a function of relative distances between the near and far objects. In portraiture shooting from further back will make the nose appear smaller relative to the ears in an full face pose, or when the face is at an oblique angle make the far side of the face look larger than it would relative to the nearer nose when shot from a closer distance.
All faces are different shapes, some more naturally symmetrical than others, and part of finding the most flattering look involves looking at the five "prime" views of a person's face -- left profile, left oblique, full, right oblique, left profile -- from different shooting distances to let your brain, by comparison, tell you which is most flattering. WIth experience you'll be able to look at a face and know when shooting from further away with a long lens would be more flattering.
The conventional wisdom for portrait FL of 85-150mm is based on a FF 35mm camera producing in camera crops ranging from loose H&S to tight head shots from a distance of around 8ft, which produces "normal" (as seen by eye) perspective. With the 300mm you will find that by the time you get far enough back to get the desired in-camera crop it will be so far away that noticeable near/far size distortion will be evident.
Chuck
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