Well, I've done it. I've finally ingrained the necessity for middle-men and information brokers so deeply into my players that they now seek to consolidate these functions into as few people as possible. Namely: the barkeep of the infamous Taberna Poveri Homini, Lukius, has become their go-to man for hiring mercenaries. Due to his contacts with the world of swords-for-hire they rarely rent out heralds and do interviews anymore. Rather, they nominate him as agent, pay a large fee, and let him negotiate the price with the mercenaries; he keeps whatever he can save of his fee while, of course, still fetching the best hirelings money can buy.
Two characters are playing with very socially-integrated kits this time round. Mike is a Knight of Miles and Steve is an Imperial Schoolman. These two kits grant them access to various social graces as well as a number of resources—in this case the library and scholars of the Imperial Schola. Since the Ironbreakers are attempting to clear a ruinous tower's laboratory floors (sub-levels located below and attached to the ancient sewer systems of Miles) that are crawling with various types of oozes and slimes, they sought out aid from one of the scholars of strange and exotic creatures who resides in the Schola and got all the information they could about the various creatures. This use of sage knowledge has certainly payed off, at least in the planning phases.
So what's my point? Well, bartenders and 'keeps have been traditionally the repositories of local knowledge and wisdom in fantasy works. Though permanent taverns are poorly attested in medieval sources, we can see how the logic fits: everyone likes to drink, when they drink they talk, therefore they talk most at the tavern (a place where everyone goes). This leads to the barkeep becoming well acquainted with most people in his social circle and thus makes him a font of useful information. This is more reminiscent of the 17th and 18th century tavern than it is of any truly medieval establishment, but it's useful as hell to players.
Assuming the trope of the tavern-as-information-broker is true, Lukius takes this to a whole other level. Namely, the Taverna Poveri is an adventurer's bar where adventurer's go. This means things that are likely to crop up there include: people looking for adventurers, knowledge of how and where to get employment as a mercenary, and services that target adventurers specifically, such as small platoons of fighting folk looking to hire on to a party. This semi-centralization both serves to deconstruct the classic tropes (which themselves were very self aware) and provide a more localized place for adventurers to get their information and hirelings from without having to think too long and hard about the realities of a medieval city.
That being said, I justify it because Miles has a population of ~3 million mostly fed on imported grain, and is the largest city in the setting as well as the center of trade and culture in most of the North. While you won't find permanent taverns with connected barkeeps anywhere, if you are going to find one somewhere, it's going to be in Miles, and it's going to be on the infamous Adventurer's Stair.