I'm happy to help
The "insert picture" menu item stays grey until you Direct Connect to the screen name you want to insert a picture for. To do this, click on the button between
link and the envelope.
Once you click on that button, a small window will pop up notifying you that you're attempting to DC to that person. They must accept when a window pops up for them requesting the DC. It can take up to a minute to connect, so don't cancel it. If it doesn't work after it tells you that you were "unable to connect", ask that person to click on the button, and then YOU accept. Sometimes you have to ask the other person to initiate, and then it works.