I by FAR am no expert on anything about bicycling (except I am getting pretty good at falling it seems), but I say go clipless and don't look back.

Yeh, it takes alot of getting used to. Especially if you are timid like me. I have ZERO confidence and it shows, but being clipped in definately makes me more efficient of a rider. I am able to utilize different muscles if I want. I am able to make any numbness my toes might get go away without removing my foot from the pedal (before I would have to shake my foot out to ease the numbness). My feet don't slip off the pedal anymore when I go "fast" (I use that term loosely) which helps me maintain my speed instead of losing it.

I have regular Shimano clipless pedals that came with my bike. I got the Shimano mountain shoes versus the road shoes because for me, I want the ability to walk in the shoes without having to carry a pair to change into when I am not riding. They make a slight "click" noise when the cleat hits pavement but its not terribly annoying. And they look normal enough. In my experience, they are very true to size.