Wow, if I was reading this as someone who was not using clipless, I would *never* have started using clipless!

Multiple painful encounters? Multiple falls in a week?

Everyone I know with the exception of 1 particular person who has learned to use clipless hasn't gone through all of this at all. They got clipless pedals and shoes, started off with a few slow rides where they didn't push it until they got used to clipping in and out, and never suffered any of this "serious pain". Most of them (including myself) had exactly 1 fall - they came up to an intersection, slowed to a stop, didn't quite unclip in time, and slowly toppled over bruising nothing but their ego. :-) No series of pain, no multiple falls, etc.

The 1 and only person I know who's had multiple falls is just sort of reckless. He threw his new pedals and shoes on the bike, rode off full speed, and never took any time to try to learn the clip in / clip out thing. He's had multiple falls, one was rather painful (though he's never broken any bones or anything serious like that, to be fair). It was kind of funny actually, another friend of ours rides dirt bikes, and this guy wanted to go with him and our friend was like "Noooooooooo way man. You'll kill yourself! You're not the kinda guy who's going to learn to ride the bike before doing something stupid!" lol.

You absolutely have to take the time to ride cautiously and learn to clip in/out of clipless pedals automatically before you start riding hard again. But if you do, you shouldn't suffer more than a single bruise to your ego one time when you come to a stop and don't quite unclip in time. But - that's it. No multiple falls, painful experiences, etc. On average.