The really neat thing I am finding about this forum is how much we all have in common as cyclists. We have similar needs and questions, similar experiences. Experiences to pass on etc.
So I chuckled at your questions about going clipless and then at reading the answers.
My two cents:
1. You will love riding with clipless pedals and you will wonder how you ever road without them.
2. You are going to fall a couple times. No spectacular crashes to brag about latter. No, you will fall from a near stand still either at a traffic light or when your companion stops and you pull up to do the same. And most importantly, you will feel like a complete idiot and of all the people who turn to look, the ones nodding in sympathy are the ones who have been there too, bro.
sth