The Avatars for personalties show tiny picture of a pawn and not the actual photo you see when selecting opponent. Is this normal?

The pawn icons indicate which player is White and which is Black. If you don't see the personalities pictures, then the Game Status window is too small. You need to make it bigger (i.e., wider). Then you'll see their pictures instead of the silhouettes.

You might want to read the Chessmaster Grandmaster Edition FAQ...

I made the game status window larger and now I see pictures of my opponents.

Thanks for the info!