TallIan
Explorer
The other issue is Sleep deprivation is more heavily a "willpower" focus, which now falls under the purview of wisdom saving throws. I can understand why you wish you could simplify it down to a Con check, but it's really not a physical endeavour to stay awake, but a mental one. Feeling "so tired" because of a lack of sleep is more because your brain is struggling to cope, as opposed to your body.
If you want a simple thing, I'd go with:
You can stay awake for 24 hours with no effect, after which a DC 15 Wisdom check is required to stay awake. After 48 hours awake you suffer disadvantage on all checks and cannot concentrate on spells.
Physical fitness does play a major part in how well you cope with the lack of sleep. Willpower comes into it when you push past that need for sleep to try and achieve something, ie "I'm too tired to bother cooking and eating or making a proper camp, I'll just sit here in the cold and rain."
The first 24 to 48 hours are not that hard, though people not suffering from sleep deprivation will notice your ability to perform decrease. The bigger issue is getting through quite periods - especially in the dark.
..., I would seriously consider not allowing recovery of anything from a short rest either, if the characters have gone at least 24 hours since the end of their last long rest.
Actually frequent short rests (not talking about the 5e mechanic here) become MORE important.
I would probably stick with CON saves. Assuming a start time of 08:00 day 1
Check to stay awake, if they aren't active at:
03:00 Day 2
18:00 Day 2
Midnight
03:00 Day 3 and then any time they stop, (even for a few minutes)
From nightfall on day 3 a CON check every night, if they fail give them a -2 penalty to all checks for thie first failure and then a level of exhaustion for each failure after that.
Tall