Quote from: CRKrueger;1012299Here's a shock to everybody I know: I like downtime to arise organically from within play and make sense within the setting and not be an externally mandated "cycle" of play.  In MERP I had characters winter in Rivendell one year and once they hung out with Beorn's great-grandson recovering from some wounds: we didn't need any mechanics to do it.

Same here. One reason I like 5e D&Ds downtime stuff is its mostly either answers to basic questions like "how much does rent cost at this living threshold?" or things to handle offscreen sorts of events, player initiated events, or just a quick what the hell happened. Owning a business, shopping a magic item, making something, living expenses, random partying, etc.

Alot of that is things the players decide to do. Not something the game mechanics mandate they have to do. And the rest is just simple RPing.

It depends: is there stuff going on during the downtime that could possibly affect the PCs? Are there things that might happen?

If the former, then obviously the PCs have to react to those in some way. If the latter, then random rolls are called for. If there's nothing of relevance happening or having a chance of happening, then you entirely go by what the players want their characters to be doing in the downtime, though obviously you have to decide there whether some rolls or even a side-session is required.

Of course. The players decide to send the PCs off to sell a magic item. In 5e D&D you might want to roll to see how long it takes, then how much is offered, and if you are feeling like it, roll for possible complications which Xanithar's Guide adds. A seemingly simple action can end up cascading out of control now and then.

I've almost always made or seen both modes available depending on what people want and what makes sense for the situation. In some games, such details are more or less out of scope and so more or less never get played out. I've never seen a game of much length where all stuff had to be played out in detail. Sometimes it can be tedious and needless and take a lot of time, and sometimes it also means some players are waiting around while others shop or socialize. So there's some balance that the GM might do well to feel out, allowing details when wanted or needed or when it adds something, and scaling it back when it's not adding much.

It also really helps if the GM is good at assigning appropriate chances for interesting things to happen and for PCs to notice them, and rolls and describes what PCs notice appropriately. e.g. there will be some chances of getting noticed, jipped, followed, pickpocketed, mugged, making new acquaintances, discovering something interesting, etc., even when just going to water the horses or buy more food, which a good GM can assess, make appropriate perception rolls, and describe appropriately the right level of detail and information for each.

Usually I and the good GMs I've played with will allow players to play out things if they want to. To me this is part of letting players explore the game world and pursue their own interests, more or less whatever those are.