NO such thing as a dumb question no matter how long you been playing

In answer to your pic probs. When you first start ootp, click settings and click the 3D Facegen tab and set the last option to search for picture first.
Then in game click the game tab and then click the Players&Facegen tab. Set Player Pictures for to All Players
Set Create Player Pictures to On demand.
Set Update/Generate Player pictures to Always if needed.
Set other options as you prefer.
Real pics will now load automatically and as soon as you click on any player that does not have his real life pic or the game uses him, he'll get a facegen pic.
Best of both worlds