So Your Players Want to Run A Tavern

At some point, your players are going to want to run a tavern. This is inevitable. They may be inspired by Dragonlance, possibly their favorite detective novel, but somewhere along the line they're going to want to try their hand at running a bar. It looks simple, it's a great way to find adventure, and it ensures that you have all of the ale you can drink; all told, this is not a bad way to spend some downtime. However, this does not mean the referee cannot use the tavern against them.

[Note that this applies to any business venture started by the players, be it a weapon shop, a university, or even a merc outfit. It just seems that "tavern/bar" seems to be the most popular choice.]

New Role-Playing Opportunities

We're going to assume that setting things up was relatively easy, but the interviews should be fun to role-play through. However, the real fun comes when the business is set up; the PCs now get to deal with the customers. The PCs should notice an interesting change in the bar-fight dynamic: They used to be the ones starting the fight, or at least seeing what they could do once it started. Now, they're the ones trying to stop the fights as soon as they start. This applies across the board: They get to deal with the drunks, the surprise inspections from the town guards, and even setting up competitions and making the cheaters are caught (rather than doing the cheating).

This also means that they're going to be dealing with the next rung of people: the merchants and guild masters. They're going to need to keep the tavern stocked, which can be an adventure in and of itself. Broken furniture and glasses need to be replaced; this means dealing with those artisans. Looking for some special decorations? More artisans. Is it a realm where magic is a thing? Then you're going to be dealing with mages to set upwards and do the pest extermination. You may not need to deal with modern codes, but it doesn't necessarily make it easier.

If You Thought The Competition Was Tough Before

The competition has now changed as well. In theory, the PCs are now legitimate businessmen; this means that they need to compete with the local inns and taverns. That competition can be cutthroat especially if the area has its own organized crime family who doesn't like the new competition; they need to decide between taking them out and paying the protection money. They also need to debate how they'll handle corrupt guards and officials looking for bribes. They also need to deal with their competition, which can get nasty as well; arson and other inconveniences are just part of the hazing.

Throw fantasy rules into the mix and it gets worse. Evil priests can make any food or drink a disease carrier, ticked-off druids can summon pests, birds, and raccoons to bedevil your tavern, and sorcerers can send all sorts of minor demons and elementals your way. Cursed items and delayed spells come into play; delayed fireballs and toad statues that sour milk become a legitimate concern. It only gets worse when you realize that the enemies and rivals that the PCs had are still coming after them and they are picking up new ones.

Life is only as boring as the assassins' guild lets it get.

If You Thought HOAs Were Bad

Then there are the obligations of just being a business in a medieval setting. Citizens were expected to help defend the town in emergencies, becoming part of the bucket brigade and militia. Theoretically, this means that the lord-mayor of the town can draft any townsman for necessary jobs, and the PCs represent experienced assets; the PCs could find themselves on a mission for little to no pay as a result of their duty to the town. There are also the yearly taxes and fees, as well as the "voluntary tariff" to pay for the militia's weapons and rewards for bounties. As with bar brawls above, the adventurers may find themselves in the position of defending the town hall instead of invading it.

This all ignores that the local merchants may meet regularly to set prices and deal with mutual issues, or that they may need to deal with some sort of zoning laws (taverns are only allowed in specific locations, for example). If the competition doesn't get to them, their new obligations as business owners may.

So while the players are no doubt thinking that running a tavern is going to be all sorts of fun, they aren't thinking of the possible complications it's going to cause. It is up to you to remind them of that, preferably as painfully as possible. However, keep in mind that you should still strive to keep the tavern fun; even if bad things happen around, and because of it, it should still be a haven of some sort. So have fun with the idea, be aware that it's eventually going down in flames (preferably gloriously so), and let them enjoy it for as long as possible.