As far as the controversial "don't use handloads for self defense" Ayoob has produced a couple of specific cases where they caused legal problems. So the risk of handloads causing problems is low, but not zero.
In what way did it cause legal problems?
Was it an actual factor in the outcome of the case or was it something the lawyers just talked about?
The best known case is probably New Jersey v. Daniel Bias - which did result in a conviction. I'll let you Google, as it is extensively discussed in several places.
