One of the relatively few things that bothers me a bit in D&D 5e Basic is the decision the player is presented with during a short rest of how many hit dice to recover as a result of the rest. As people who’ve been following along know, I really prefer “diegesis” in my game mechanics… that is things that present decisions and options from the character’s point of view*.
So while I don’t particularly object to the notion that the characters can get a substantial part of the HP back after a “Short Rest” of an hour or more, I have a bit of trouble picturing what it is the character is deciding when recovering 1 vs. 2 vs. 3 Hit Dice. It’s not the end of the world, but it could be cleaner.
So, let’s fix it up:
After a Short Rest, a character regains 1 Hit Die (assuming there are any left… ) In order to regain more than a single HD, the character has to take extra steps to make the rest more comfortable and complete. Each extra step is one more HD recovered. A non-exhaustive list of extra steps might be:
- Take off armor,
- bandage and clean scrapes and cuts,
- drink something,
- drink something alcoholic,
- eat some food,
- drink a hot beverage,
- eat some hot food,
- take a cat-nap,
- sit around and chew the fat with another PC or NPC (must be roleplayed, and should be idle chatter about backgrounds and such, rather than tense planning about next steps and tactics),
- play a musical instrument or sing,
- huddle around a fire,
- clean weapons and maintain tools,
- take off boots,
- bathe,
- take a hot bath,
- shave,
- smoke something,
- canoodle,
- write a letter to someone left behind
In other words, just about anything that might be depicted in a story showing the characters in their down-time. (Things like drinking a hot beverage are intended to be allowed to stack with drinking something; this is deliberate to allow recovery of bigger chunks of HD for higher level characters without making them list a dozen things they’re doing.) The characters can thus have a reasonable proxy for the decision of how many of their HD they recover by deciding just how relaxed and unready for action they’re willing to become to knit body and soul back together. In addition this will hopefully lead to slightly more vivid descriptions of what the characters are doing during their Short Rest.
This doesn’t really change any of the game mechanics of Short Rests at all, it’s just a way of tying it more tightly into the fictional world.
* It’s my usual complaint about Fate or Luck points: is it something the character knows about in the game world? If not, then it can get in the way of my thinking about what the character would do. As the player, I might know that since I have a Fate point to spend, the character will absolutely be able to hit the fleeing villain with a shot without endangering the hostage; the character, though, probably ought to view it as a real risk. Whether to take the risk ought, imo, to depend on my take on how bold or desperate the character is and not whether I’ve got or can scrounge some meta-game resources to reduce the risk.
Tales of the Rambling Bumblers 
I like this quite a lot. It reminds me very much of Torchbearer. My only possible quibble is that a few of these would be exceptionally weird in the midst of a dungeon, and make more sense during a long rest, or even more as part of the Recuperation downtime action.
Actually, I’m kind of hoping that the fact that some of them would be weird in a dungeon will keep people from doing them… then instead of having to make an ad hoc rule on how much they can get back from a Short Rest in hostile territory, or tweaking the encounter tables to make it unlikely they get through one, I can rely on their sense of what’s plausible in the genre to either keep them from trying or make them come up with clever alternatives that don’t strain credulity.
At the end of the day we are playing a game. I personally don’t think these meta details really hurt anything. Because it is a simulation and not real life it is unrealistic to think everything needs to be, well realistic. Personally instead of worrying about where/how many hit die a players getting back I’d rather just be playing.
That being said I do like the flavor you are adding to the short rest, but I’m OK with leaving it up to the players as to whether or not they want to turn it into a role-playing opportunity or not. The insta-heal of Dungeons and Dragons 5th Editon is my only gripe so far. That has more to do with my preference for a grittier game than any real problem with the rules as per the way WOTCs now defines HP.
Since I personally am bothered by these kinds of things when I run into them as a player, I think they really do hurt at least some of the time.