It's been hit-or-miss for me (Firefox w/ uBlock). It seems like Google's pushing updates at irregular intervals. Clearing the uBlock cache and forcing an update usually does the trick for me, though. I'm guessing they'll burn the volunteers out eventually, though.
Clearing the catche and forcing an update seems to work but I'm not sure it actually does anything. I think they're just slowly ramping up the frequency of that pop up. For me atleast it has just been getting worse and worse despite all my efforts.
Yeah, updating it only does something if the uBlock team pushed an update that addresses Google's recent push. I've been lucky so far where I've only ever had to update after they released an update, but you can get unlucky and have to wait for an update.
I haven't but I can make it appear by turning on the Block ads feature in YouTube Enhancer (so no one can tell me it's "slow rollout"). So far Filterlist devs are doing a great job at blocking them, just like they always have on every website that is commonly used and isn't a malware or scam site (not great examples of Anti-adblock sucess since they're usually added to malware filters once detected).