Bike shoes - On in transition or clipped to bike???

Just a matter of personal preference I think.  If you're doing a sprint tri then you'll likely save time by leaving them clipped in.  If you're doing an HIM or IM then the few seconds it saves you probably won't matter....unless you're a pro.

I put my shoes on and run with them - but that's just me.  I've never had an issue with the clips breaking or jamming up.  If you do end up deciding to leave them clipped in, then the best advice I could give is practice, practice, practice.  I've seen plenty of people bite it during a running mount and I've seen just as many (including myself) crash during a flying dismount

+1... definitely practice first on a *soft* surface like grass while going slow.  When I first practicing flying dismounts, I completely bit the dust a few times.  Biggest thing that helped me was actually trying the flying dismount with normal running shoes first and getting the motion of swinging your leg over and then putting your foot down and running with your bike without having to worry about getting your feet out of your shoes.  Then, progress up from there.  To some people, it comes much more naturally; others it takes much more practice and coordination.

I'll add that flying in with the shoes clipped in scared the heck out of me, to the point that I went with MTB shoes over road shoes so it would be easier to run from T1.  I've decided that 2011 will be the year of more speed (I had 2 AG 4ths last year by less than 4 seconds behind 3rd), so I upgraded to tri shoes and clips.  I've simulated the mount and dismount each trainer ride this Winter and, if the weather ever breaks, will be practicing in the grass and moving up to pavement as I get comfortable. 

On a realted note, anyone see the Tri Clips ad on Facebook?  I watched the video and I could see those things getting wrapped in the rear spokes.  Seems like thin rubber bands are still the best option.