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I wonder if this maybe depicts one or two establishments from Pathfinder Campaign Setting: Inner Sea Taverns?

Bellona |

The hilltop/mountaintop gambling hall looks like it has a nice view, but ... all ... those ... stairs! I imagine that spellcasters can make a financial killing during their downtime just with Dimension Door spells and the like.
"Departures every 15 minutes from the base starting at 11:00, from the top starting at 11:20. Last trip up at 02:00, last trip down at 02:50!"

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I really can't use any flip-mat where horse-boxes are 1 square broad.
These mats are designed for use with miniatures and ALL horse minis are 2 x 2 squares.
Also in reality horses may be transported in such narrow trailers, but they are not standing in such small stable-boxes all day/night.
In the real world this would fall under animal-cruelty, in the fantasy world of Pathfinder it's just annoying.
Now if there would be a medium sized "Pony" miniature, i could use this as a tavern for "small folk", but there isn't any.
Rant off.

James. Long |

I really can't use any flip-mat where horse-boxes are 1 square broad.
These mats are designed for use with miniatures and ALL horse minis are 2 x 2 squares.
Also in reality horses may be transported in such narrow trailers, but they are not standing in such small stable-boxes all day/night.
In the real world this would fall under animal-cruelty, in the fantasy world of Pathfinder it's just annoying.
Now if there would be a medium sized "Pony" miniature, i could use this as a tavern for "small folk", but there isn't any.
Rant off.
Back when miniatures were first a thing, the horses with no base broke legs off, and the ones with a skinny base tipped over. That horse was invariably a captain, and knocked all oh his troops over. That's why a SINGLE horse has a large base. Look for the horses with clear bases.
So way back when these first became popular.. it was actually a third party company that came out with the miniatures rules to use alongside D&D. The majority of it was about placement, location, range and stuff like that, so there's no reason you couldn't adapt it to 5E.
I mention it because various large and huge items have REALLY big bases that doesn't work in game play. For this reason, a single horse is considered to take up 1x2 squares. a team 2x2 and a team and a coach 2x4. The bases are to be considered as nonexistent in game play. For this reason, you're supposed to actually own single horses, teams and carriages in order to be able to place them properly on the map. Generally speaking, if the miniature is ACTUALLY to scale, it is considered to occupy the squares that it ACTUALLY occupies, not the size of the base.
The simple solution? Don't use miniatures. Convert to a VTT. FoundryVTT has two different third party people making sensor systems to use physical miniatures ON a VTT.

David knott 242 |

By the rules, non-square/non-circular bases have not been a thing since D&D went from D&D 3.0 to D&D 3.5. I am pretty sure that they were eliminated after it became obvious that such base shapes implied a facing, which was clearly eliminated in D&D 3.0. With the exception of some optional rules in the D&D 3.5 Unearthed Arcana, no follow-on rules have restored facing or rectangular bases. As a result, moving onto the base of a large creature is squeezing if they are friendly and just plain illegal if they are not.