It seems like it would be nice to have a better classification system for the challenges a particular terrain poses. While having videos to see what the trail looks like is definitely a step up, it seems like a pain in the ass to have to watch someone walk it (and it would ruin a bit of the wonder for me, personally). I wonder if it's possible to condense the terrain down to a series of "potentially problematic features". I'm not an expert in accessibility, so I don't know what exactly one would flag, but things that come to mind would be rough terrain (inaccessible by typical wheelchair, accessible by ruggedized wheelchair), rough terrain (inaccessible by any wheelchair), non-smooth terrain (debris on trail could trip someone, accessible by any wheelchair), gradient in excess of X%, whether the trail is shared with bicyclists, etc.
I do worry about the data the operator would have access to, though. And even if we assume the operator is above reproach, I would worry that hackers would get access to the data. It's not something that I would want to host personally, just because of the risk of causing harm if the data were to be stolen.
I think it's more important to have the information available. I might not go to a place with a step at the entrance by myself but if I have people with me I can decide that I'll risk it.