I am a recent clipless convert! I picked up a geared bike with look pedals and found some new w/o box shoes with look delta red's for $35. I figured for that price, if I really don't like clipless, I didn't really put in a large investment.

Clipless makes you feel REALLY connected to your bike. I used to worry about foot-pedal placement alot but with clipless, you never have to worry about it once it's setup. Also, unclipping isn't really an issue. You might fall the first ride b/c you forgot but unclipping is almost natural once you get the hang of it. Now that I like it, I can invest in a better setup. I'm thinking SPD is the way to go for me (alot of walking & errands).

I'm looking at these Shimano PD-A530 b/c:
1. SPD setup is nice for wearing one pair of shoes. Riding, walking
2. If I don't have my riding shoes, they're platforms. Still rideable
3. My friends and I sometimes switch bikes while riding (they only use platforms). This way I can use their bikes and they can use mine.