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I know there must be a reason that lodging costs money, but I'm not sure what that means mechanically.

My players have been doing a lot of napping outside because they don't want to pay for a place to stay. I know that the most hard-and-fast solution is "roll for random encounters and ambushes while they sleep," but they've actually been napping in relatively safe urban areas, like on park benches or under trees, or behind fences on the property of the people who hire them (without being noticed). I also know that a long rest doesn't count as a long rest unless the 8 hours go uninterrupted, but I really have no justification to say that they wake up or are bothered in the middle.

My Question: Is there a mechanic for a "bad night's sleep" or sleeping without a bed in general? Where can I find more information on this?

(My "GM common sense" says that failing to get a good night's rest has consequences—it does in real life, and that's how I'm going to run it. I just need to know if there's a rule for that. If there isn't, I'll just homebrew it.)

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There aren't rules, but there are some guidelines and boundaries...

I think you'll have an easy time interrupting a long rest (and thus denying the benefits therefrom), but going into the exhaustion mechanic seems too much. But interrupting even one night's rest should be a lesson to the characters: day two of encounters gets pretty tough, and looking ahead to a possible third day without a long rest should be enough to drive them inside. They're not paying to get the long rest, they're paying for assurance that they'll have a long rest.

Below I detail the rules and scenarios that inform my thinking.

Resting

For a long rest RAW requires at least 8 hours: at least 6 sleeping, no more than 2 of light activity: reading, talking, eating, and standing watch are the examples given. 1 hour of walking, (any) fighting, casting spells, "or similar adventuring activity" are examples of what might ruin a long rest. (PHB p.186)

Exhaustion

The next touch-point we have on the spectrum is that of exhaustion. At the mildest level of exhaustion one incurs disadvantage on all ability checks.

The general description refers to starvation or extreme (freezing or scorching) temperatures (PHB p.291). Further, under Travel Pace we see that the ninth, tenth, &c. hours of a forced march become progressively more-likely of incurring exhaustion (PHB p.181).

Two examples from D&D Expeditions modules also come to mind, one from season 2, one from season 3:

DDEX2-4 Maybem in Earthspur Mines requires the characters travel through a blizzard for approximately three days. Failing a DC12 CON save will gain characters 1d4 exhaustion levels. So three days in a blizzard might get you no exhaustion; might get you disadvantage on all checks, saves, and attacks as well as halving movement and HP.

 

DDEX3-2 Shackles of Blood lands the characters in a prisoners' caravan where the guards provide them only moldy bread, fetid water, and the guards "jab at prisoners with sticks to pass the time." The journey is "cramped and uncomfortable." Unless the characters alleviate these conditions, they will arrive at their destination with one level of exhaustion.

From these general guidelines and specific examples we see it takes a good deal--much more than an uncomfortable night's sleep--to incur even one level of exhaustion. So the exhaustion mechanic would seem horribly overpowered for your park-sleepers.

Encounters

Recall that encounters don't have to be hostile, and don't even have to bear sentient features. An encounter might just be the lamplighter coming by to douse lamps. Or a caravan of fish coming up from the docks at 4am. Or the night-rending sound of tomcats fighting for territory. Or a few hours' cold rain (good call, @GMJoe). Any of these--and certainly a few of them--could reasonably turn a long rest into a couple of short rests.

And a "relatively safe" urban area certainly has a militia or constabulary--or gang!--making it so. If you're not getting pick-pocketed or stabbed, it's got to be because the local authority is keeping a lid on those problems. And you're "those sorts of problems."

Economy

A night's lodging has a price. What are your characters paying for when they purchase a night's lodging? If you can answer that, you know what to take away when they eschew a roof and a bed.

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    \$\begingroup\$ +1 for the watch waking you up and demanding to know why you think it's acceptable to sleep in the Duke's Park. \$\endgroup\$ – GMJoe Feb 7 '16 at 23:42
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There are no rules for quality of sleep, however camping out in urban areas has just as much risk as camping in the wilderness. You simply have different sorts of encounters.

If they are camping in the park, perhaps a constable or city guard makes them move along say 4 hours into their nap, or perhaps the local rogues take a chance at nicking some of their shiny things (which they may not wake up and notice this they get their rest, but something valuable for the players' or party's success is snatched.)

Or perhaps the people who hired them don't really want the neighbors to see they've hired scoundrels, proper folks have proper accommodation don't ya know!!! The scandal!!!

Maybe if enough people notice, the townspeople themselves start to ask the vagrants to leave town.

There are lots of possibilities to reduce the benefit of sleeping out of doors all the time. Just be creative about how to handle it and encourage the players to spend coin on something other than gear. Maybe it's loosing sleep, maybe it's loosing property, or maybe it's loosing reputation, but make it hurt a little, not a lot but enough to alter your party's choices.

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The short answer is no, there's nothing in RAW that gives any advantage to one lifestyle over another when resting. The closest thing to it would be the last paragraph on p. 157:

Your lifestyle choice can have consequences. Maintaining a wealthy lifestyle might help you make contacts with the rich and powerful, though you run the risk of attracting thieves...

So the extent of the rules is just that guideline for players and DMs.

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    \$\begingroup\$ This is by no means RAW, but I houseruled this a little bit for my campaign here; if you're looking to homebrew, it might help (though this assumes much longer long rests): polisurgist.github.io/Up-From-the-Mud-Wiki/en_US/#!pages/… My eventual goal, in a campaign that has a lot of downtime between adventures, to have a sort of "random encounters" table based on lifestyle, where the random encounters are more favorable the higher you go on the chart. \$\endgroup\$ – Polisurgist Nov 22 '15 at 19:22
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There are rules for this!

In the 5e players handbook, under chapter five, there is a subheading called lifestyle expenses. This details some possibilities on how people should expect to live depending on how much they pay and provides some good tips for doing so.

Some examples I can think of: For instance, perhaps the town mayor had an important mission to undertake, but when these "heroes" living in the street, with rumors being spread about them, in full armor, show up, he may refuse out of distrust.

Also, sleeping in armor is incredibly uncomfortable. Even leather is hard and rigid in armor, and if they try to sleep in it they could suffer from exhaustion because of no good sleep, and if they take it off, they could wake up with it all missing next morning! Think about what would happen today if a bunch of people just showed up in a suburb and started living on the street. Real consequences are almost always fair and immersive, except in extreme cases

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    \$\begingroup\$ Those aren't rules for what different lifestyle levels actually mean, though. \$\endgroup\$ – Polisurgist Nov 22 '15 at 19:07
  • \$\begingroup\$ No, it's chapter 5, and they don't cover those. They were suggestions. And yes, there are. Chapter 5 right after equipment \$\endgroup\$ – Nemenia Nov 22 '15 at 19:10
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    \$\begingroup\$ (I was looking at the wrong book, DMG chapter 6 covers lifestyle) \$\endgroup\$ – Tritium21 Nov 22 '15 at 19:14
  • \$\begingroup\$ It's alright. I did fix the suggestions section \$\endgroup\$ – Nemenia Nov 22 '15 at 19:17
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    \$\begingroup\$ The rules you point to do not give any mechanical disadvantage to not sleeping in a bed - or of any lifestyle at all. \$\endgroup\$ – Tritium21 Nov 22 '15 at 19:17

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