I've had this idea, to ask my future landlords about the mistakes of past guests. Just to get a sense of their peckadillos, the little things about the place that people don't know, stuff like that. Maybe employers as well. But this is something that's setting off my etiquette alarms. Maybe this isn't a source of wisdom so much as a source of awkward moments?
On the one hand, if you don't know them yet, and haven't had any time to make mistakes, it's pretty clearly not something that could embarrass you. Obviously that's the most important thing. You can't put someone in that position, because them embarrassing you might not be the worst case scenario. Worse would be they have something important to tell you, you think they would have, but they were polite, ignored the prompt to impoliteness, and now you are confidently bothering them.
But the obvious next problem is, asking them to embarrass people they still know and do business with. Mistakes of coworkers are, essentially, none of your business, not during a first-ish-day conversation like this. Even asking the question "what have other people in this role done that you've not liked?" might come across as trying to drive a wedge between them, which is a bit odd. And if you rent a unit, they might have others, and they're your neighbors. You don't want it getting back to them you're looking for dirt.
That being said, it seems these problems are avoidable. Be extremely clear you're looking for categories of insight, and general knowledge. Procedural stuff. Or ask for any time someone got embarrassed and ask for that wisdom, because you know you'll embarrass yourself the same way. Maybe that makes it clearer what the upside is for them.
Any suggestions for improvement would be helpful. This might end up, in some form, on my getting-to-know-you-in-business checklist, so stakes are decently high. I'd like to get the etiquette right.