clearstream
(He, Him)
I've used it in practice fairly frequently. Notably where the party chose to have a scout travelling ahead of them during overland movement in the tunnels of Underdark, and later on in the jungles of Chult. In such places, Skulkers and Wood elves readily find conditions suitable to hide in. On occasions one check would stand for a good part of a march: perhaps a couple of hours.Of course, "in principle" does not mean "in practice", which is where I think I've been getting hung up. If a player declares their PC will continue to Hide after assessing the environment, the DM needs to adjudicate accordingly - enemies could start actively searching, the terrain could change from one area to the next increasing the chance of making noise, cover could be compromised, etc. "Stealth rides", IMO, really means that the player doesn't have to roll again to maintain their hidden state as long as no other conditions in the environment have changed that threaten that state.
There is a question in my mind about corner-cases where a hidden observer spots said scout and chooses to stay hidden? In OOTA the party is pursued for the first half of the campaign so that is a situation that can arise more than once. I chose to let the scout's check continue to stand, although one could have argued that as their stealth was broken - for that observer - it should have ended. Stealth is an interesting case because one check ends up setting a DC for multiple possible observers.
I see such cases as relevant to the OP, because reflecting on them can yield insights into how to calibrate DCs. Perspectives to view that from.