danz, I'd definitely like to hope that things will fit better once a proper key is installed, but I am pretty concerned about the condition of that crank snout...
Ian, that sounds like a pretty indestructible setup! Depending how this all plays out I may have to consider that as well. Though so far I haven't had any bolts break. Of course, I've only driven the thing a few hundred miles since I bought it last year. I did not expect I was getting into this big of a mess. Sigh.
Kevin, that's a good point that I hadn't caught. It's even more visible in this picture:
It does appear that the wear in that direction is minimal enough that the pulley still seats onto the front of the sprocket, and not the crank- This is what it looks like fully pressed on (though not torqued, of course). The alignment is probably still garbage, though:
Your recommendation of a new crank is very much what I was afraid of. I feel as though that's somewhat beyond my current capability and equipment... Or is it not as bad as I expect? Is it possible to accomplish while the engine is still in the car?