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1. What is needed to start a guild?
Depends on the location. Most kingdoms or great cities will require you to register or get the ruler's permission (or a council of nobles or guilds or even other mercenary companies). Obviously some companies can have branches or guildhouses/halls in multiple lands and cities, but you likely have to pay a tax or tithe or deal with the ruler. Most don't want a lot of armed, trained soldiers that aren't necessarily loyal to them, unless they're often doing jobs that help the kingdom, like clearing out monsters.
You will usually need a charter, that is a list of rules or duties or tasks or expectations (possibly a motto) or something that conveys the goals or ultimate purpose of the guild.
Then you probably need a home base or location. At first it could just be the backroom of a tavern or a warehouse that one of the guys watches as a security guard. But generally a place for the members to gather.
2. What is the structure of a guild?
Depends on the guild. There's as many structures as there are likely governments. Usually a guild is a guildmaster, some senior members, treasurer, quartermaster, sergeant-at-arms, and members or associates. But it depends on the guild. A mercenary company likely has a commander, and a second in command, a quartermaster, logistics people, senior ranks or leaders, likely depending on their squad or how many people they command.
3a. Are there fees to join?
For most guilds, yes. That's because in most settings guilds control who can and can't work in their territory. If you aren't a member of their guild and you're caught working without their blessing, you could be run out of town, or worse, or forced to join after paying a fine assuming you have relatively comparable skills in that craft.
It's not all bad news or mob/strongarm tactics; guilds do typically have standards and they don't want someone that isn't beholden to the standards they set going around and making doors that won't shut in a frame or building houses that might collapse because they didn't realize they needed to shore them up against a seasonal weather event or something.
For a mercenary guild, there only might be fees if the guild specifically provides jobs and actually brings work. Otherwise, most mercenaries need to supply their own gear and weapons and supplies, unless their employer is, so there isn't likely a fee unless there's a service provided, like retirement or injury payment or raise or resurrection contingencies or healing services or something.
In this case, probably not at this stage. Maybe as the guild gets bigger that can change and they can start having members pay into optional benefit plans, but those would likely be monthly or yearly fees.
3b. Are there monthly fees?
If there are tangible benefits that the guild provides. That could be how the guild rents the guildhall or space in the inn or pays their yearly charter fee/tax to the king.
4. What do these fees cover in terms of the guild?
For a member in the mercenary guild? Probably access to equipment maintenance, or simple gear, or healing services. Depending on the guild's reach or reputation, the fees could cover receiving a guild rate at some inns or wayhouses or discounts at associated blacksmiths and the fees go to cover that.
For the guild itself? The pay for their headquarters, guildhall, and charter fees, as mentioned previously, most likely. I mean... the leadership could just be corrupt and it could be paying for their gambling addiction.
5. How do the players get a cut from the jobs done?
That depends on the jobs. If they get hired by an employer or basically paired with one through the guild, the employer just pays them and the guild likely takes a cut, either from the members or from the employer when they put out the word for what they need.
Otherwise, a patron might just give the payment to the guild with the instructions and the guild just assigns someone who, if they do the job, gets the payment (after fees or whatever the guild takes). Sometimes it might just be a set contract with a base rate and the members get salvage or loot rights off foes or plunder. It really depends on the job. Obviously if you're hired to guard a warehouse, it likely will be a set fee for a set period of time, possibly with combat bonus if there's actual trouble, but likely won't be a lot of plunder in it. As opposed to a contract to sack a bandit's tower or raid a monster's lair.
6. How do [non-existent things] work?
I have no idea what you're talking about. There is no such thing.
7. What checks do I have to make behind the scenes to ensure smooth gameplay once everything is set?
Roll on Goth Guru's How's Everything Going at Work? table... or
just say things are working however you want them to be going. Unless you have some NPC just set there running the business...Roll a dice and determine what happens based on the result or how things are going. Kind of... depends on the situation going on around the world. If there's a lot of trouble or conflict or uncertainty... then mercenary guilds will be doing well. If there's not... there's less work. Then they're basically guarding things like warehouses, shipments, or caravans like any guards or doing patrols in places without an army or roadwardens or rangers.
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