[Plane]

I like the idea of a single contest where you're more likely to succeed the more things there are, with MoS deciding how many things you spot. Sounds a lot like how burst fire works. In the case of "not always the first shoe first" when you find out the number of things you spot, you could then maybe do some kind of percentile based on closeness, where the closer and more obvious stuff has a higher likelihood.

Then again, not knowing how to construct such odds, rolling individually in the first place might be easier. Penalties for simultaneous spotting should be fine so long are small and don't make the end result more likely to spot nothing at all.