I am very likely missing something deep about curved space-time, but to me, that is the same thing as grossly / coarsely seeing something cross the EH.
The fact that I can't ever get photons from at or beyond the EH and the fact that photons redshift asymptotically as they are emitted from closer and closer to the EH are measurement limitations.
If I can see the EH expand by watching what it obscures or lenses, I observed something cross it with a measurement that doesn't depend on photons from the in-falling object, no? I guess its not really a claim that I saw that "thing" cross the EH - but in principle one can measure the total in-fall over time for a BH and if one has enough information on whatever is falling in one can construct a sequence of the in-falling events.