Should Harry Potter hire an artist to paint portraits of his parents so that he could talk to them?
It might be necessary that the artist have known Harry's parents, but that shouldn't be a serious obstacle. A portrait on page 689 (759-page edition; no spoiler here) of the most recent book can speak, although it was not painted during the individual's lifetime. The portrait on page 569 was probably painted after that person's death, and folks communicated with it as well. There seems to be no necessity that portraits be made during the person's lifetime.