I concentrate on family portraiture at the moment so I cannot comment on the corporate market.
There are, of course, many variations in the answers to your questions, but what I have learned is the following:
Why: People buy portraits (as opposed to high-end photographs) as a status symbol and to have an object that will last potentially centuries (instead of years as with photos). People enjoy the hand-made aspect of portraiture. Some clients attribute a rather mystical quality to the work of "Artists", believing that we somehow "see" more than the average person and have a gift at capturing personality. Some clients buy portraits because they enjoy having original works of art in their home.
When: One of the major portrait brokers said at a conference that 65% of the entire portrait market is children's portraiture. (I imagine the majority of the remainder is corporate.) Hence most of my family portraits are of kids. I have painted commissions of children as young as two and teens as old as seventeen. Commissions come in at all times of the year. So to answer your question, there doesn't seem to be any specific "when" involved, other than before the kids are grown.
Who: My clients are affluent Moms. I reach this market by donating to expensive private school charity fundraiser auctions.
Hope that helps!
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