I haven't done clipless (i'm too cheap and forgetful). On my faster bike I have toe clips and straps, and I do have to flip things to get 'em in. I had a pair of saucony's that had the *perfect* tread - the triangles on the bottom were in just the right place to grab the pedal. Of course, the next time I bought shoes the tread was just enough different so it hit the wrong place.
On my commuter bike I have the toe clips but without the straps, which would be a lot like the toe cup. It makes it lots easier to find my way in, tho' I do still have to push the pedal over toget it on the right side, but I really like being able to get in and out from any angle, any position, quickly - commuting has its moments.
I got some Salomon shoes from steep and cheap that were made for somethign like waterfall climbing, so they have a nice stiff sole and are meshy so that when they get doused, they don't get funky. (I am also blessed with not getting cold feet easily.) The stiff sole is very nice. My next steepandcheap sneakers were Montrails which are more like regular sneakers but they're fine (adn I love their bright orange color with reflection).