Depends what you're doing. My feet were ACHING for clipless pedals the other day after I came back from the second day in a 2-day run of 65-miles each. By the end of the 65 on the second day, my little toes were chafing like no other from my toeclip straps. They're fine now, but I don't imagine my feet will be happy going a long, long, long distance over a few days.

I've stuck with toeclips largely because I have avocet shoes which have grooves in the bottom that allow quill pedals to slot into. They're really nice for vintage wear, for sure. For my spring training program they've worked well and are a significant upgrade from my ye-olde addidas I used to spot, which would make my toes numb after a while.

Really depends on what you're doing. I'd bet: <200 mi/week, don't need clipless pedals. >200 mi/week, go clipless because at that point you already have a TT Cervelo anyway.