There is no reason why it can’t, but lightning strikes are quite rare (at least ones that reach the ground are, there are many more inside clouds) and affect a small area of ground, so the chance of one hitting a place that has already been hit, (and anyone noticing!) is small.
It definitely can! In particular, aeroplanes are often struck multiple times on a single flight, and the lightening conductors on tall buildings can get dozens of shocks during a single storm.
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