OP said it starts to seem opportunistic, which I think is true, even if the party is actually disabled. Because the odds that a regular disabled person would encounter 200 unique buildings over a year that they couldn't access because of their disability seems quite slim.
And the opportunistic part comes in because these lawsuits are almost always "Fix the problem for $5*X, or pay me personally $X and I will drop the suit".
> Because the odds that a regular disabled person would encounter 200 unique buildings over a year that they couldn't access because of their disability seems quite slim.
I would guess the opposite, that 200 buildings seems low for what a person might encounter in a year that failed to be accessible. That's basically saying, "It's a roughly 4-5 buildings a week" which absolutely seems in the realm of possibility to me. Especially in a older part of town.
And the opportunistic part comes in because these lawsuits are almost always "Fix the problem for $5*X, or pay me personally $X and I will drop the suit".