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One 14-50 per bay, hardwire at least one for a higher amperage. Front or back of the garage doesn't matter as long as the cables are the full length allowed by the spec. Choose a brand of EVSE that allows power sharing so you don't need a dedicated service just for a large garage.

There are some that ceiling mount and have drop cords, but I haven't used any so can't offer advice about doing it that way.

 

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Any concerns driving over the charge cords? I’m guessing it’s not advised, but I could see that becoming a routine in our house if both vehicles are plugged in.

They are all supposed to be rated to be driven over, but definitely don't park on them, and make sure they aren't coiled up or overlapping themselves.