You know the answer to that suggestion, right? 
Make that AND an OR and you got it.
I’d also like odd shaped pads, sure.
And I’m already a happy camper that the zone fill tool at least keeps working (error message and that’s it) when I forgot to set the priority and it just drops the tool (a couple of versions back KiCAD would get unstable and not allow you to draw any new zones at all after that happened - restart needed).
So I’m thankful for what the devs come up with in their free-time - I’d be the last to feel entitled to anything here really.
I just discovered this thread, because I had a small pour under a part. Your note “or the extremety of a track must be inside the zone boundary” for it to pour solved my problem. This pour was ground on top layer, and a ground trace ran right through the center of it. And was ignored. I had to break the trace in two, terminating each segment just inside the pour boundary as noted. That solved the problem. Also, I discovered by trial and error, dropping a via to the internal ground plane caused it to fill, too.
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I think KiCad first Pours, then Checks for Connected, and the Connect-Check looks to be done on a Simplistic/fast basis. If not connected, it then deletes the pour area.
It is not quite enough that the Centre Point is inside the zone - it needs to be that the resultant polygon line centres overlap the centre. ie this adds a fill line width to that overlap rule.
It means you should draw Fill areas, well overlapping the pad centre, to auto-connect without needing a Trace.
I wonder how much more time, a more exact Connect test would add ?
Copper flood is not something that is done often, and it knows the pins to test ?