For one, because it makes absolutely no sense story-wise. More importantly, short/long rest balance.
I want the game to tell me when I can long rest.
I don't want the game to choose what I must spend my time for.
But in your case, the game is *not* telling you when you can rest, it's telling you only that it needs to be dark, and you are the one deciding if it's dark or not.
I agree the free point grinding was a bad idea. I would like to change that into a suggestion to have a character similar to Withers in the camp, whom you could pay to end the day. Wrap it into storytelling flavor of your choice. Or, heck, even reuse Withers for this. He's a super interesting character, having more opportunities to interact with him would be great. This way, you have a way out if you get stuck, but since it costs money, you are incentivized not to rely on it and to play strategically.
Furthermore, another solution I've just come up with to reduce the chance of getting stuck even occurring, perhaps the Resting Point system doesn't have to be that exact, but have more of ranges. So, say, you go from 0 to 1000 every day. You can short rest between, 200-250, 450-500, 700-750, and long rest 850-1000. At 1000 the game forces you to go to bed.
