Ovinomancer
No flips for you!
I don't understand, here. Do you check in at intervals during a rest to see if the party wants to do something else? If my players say, "We're going to attempt a short rest," then I adjudicate that -- it's the declared action. If it appears that there's no issues, it would be automatically successful, I say so, and it's done. If it appears uncertain, I engage whatever mechanics I need to resolve the uncertainty, and then it's either successful or not. If I think it can't be successful, then it's not. At no point do I do this check multiple times during a rest, short or long, so I just don't understand were this occurs.Yes. My players start a short rest, then change their minds part way through and decide on a long rest.
I wouldn't characterise this in terms of "problems" as that is evidently subjective. Rather I am interested in the mechanical implications. As I said, the case seems to rely on that first hour being the wrong kind of doing nothing...
But, let's say it does occur, because, for whatever reason, the GM has decided to check in mid-rest. If there's been no combat (or spellcasting, or whatever is ruled to break a short rest), there's no exploit, so this isn't at all a problem. If there has been combat, then the short rest was already interrupted, so, again, no problem. Either the situation is that the rest was interrupted or it was not. The only case where your issue can occur is the former -- uninterrupted rest -- and, here, there's no game issues that occur, no exploits, no nothing. Unless you were planning a combat at 59 mins and 59 seconds, but you let your players switch at 59 minutes and 58 seconds -- no, even then it's not a problem because nothing is gained by the PCs, even with this level of strangely accurate rest timing tracking.
You're complaining about an issue that has no impact on the game, but only looks to you like a strange gap in the rules. But, this really only exists at all if you allow it -- meaning that only if you adjudicate rests so that you check in with the players mid-rest to offer the opportunity to switch rest types. Don't do that and there's not even the rules oddity to worry over.