I have used Look pedals for years, from early team issue pp196's to my current Keo carbon Ti's, and I love them. As far as getting in, try this (assuming you have one foot in already, of course): The pedals will hang down with the back of the pedal in the lowest position. Put the top of the front of your foot (just about where your toes are) under the back part of the pedal and flip it over, then slide your foot into the pedal. This is easier than trying to engage the pedal just by sliding your cleat in. It takes a few days of practice and then it will be second nature (except as Hot Potato noted above, when you will be best off by taking a look down).

As for cleat wear, they are made for riding, not walking. Get a pair of cleat covers, carry them in your jersey pocket, and put them on when you get off the bike.