Generic, Text: Hirelings

Under the current RAW, players have three options for training and learning new skills:
 
If you want to learn a new language or tool use, you must spend 250 downtime days and 250 gold pieces to learn one.
The other option is to seek out special training as a reward for a completed task from a master or retired adventurer. This special train can grant proficiency in a skill or the gain of a feat.
Taking a feat through special training or as a substitution for an ability score increase.
It is just the way 5e is designed; a one size fits all balanced system. What makes this system so frustrating is that, for the most part, languages and weapon proficiencies are fluff. Stats wise, a spear and a trident are identical, with the trident weighing 1lb more. Yet, the trident is a martial weapon that only specially trained fighting classes can use, while the spear is a simple weapon available to everyone. No wait, some classes can use a quarterstaff, but sharpen the end to a point, call it a spear and they have no idea what to do with it. That makes sense, right? It makes about as much sense as a wizard dipping into one level of fighter and knowing how to use all martial weapons overnight. Don’t laugh. Play WOTC’s Curse of Strahd. The party goes into the Bonegrinder level 4 and after defeating a Coven of Hags, come out level 5. Player dips into fighter and learns every martial weapon instantly.
 
This is a pretty schizophrenic system that implies that the weapon proficiencies are fluffy enough to award them all overnight, but serious enough to require a level set back to get them. Of course the PHB says that your DM can set his own training rules. That is fixing a flaw with a DM fiat, so let’s fiat this shit.
 
First off, let’s fix learning languages. The current system takes way too long just to learn a language and completely ignores a character’s Intelligence; you know the main ability used to learn things. The U.S. government can teach an agent a language in 600 hours. D&D 5e claims it takes 2000 hours (that’s 250 days at 8 hours a day). Languages also vary in their difficulty, but that can be a call you make as a DM.
 
The Variant formula for how long it takes to learn a language is 2000/INT score = Number of days. That’s it. Now personally I like breaking languages and proficiencies down into tiers of difficulty and I will provide that at the end of this post, but it is really up to the DM.
 
As to cost, I tinkered with this system to fix a flaw I saw and to suck a little more gold from my players for fluff. Rules as Written cost for training is 1 GP a day. Which I find unrealistic considering skilled hirelings cost 2 GP per day. Personally I jack the cost up to between 5gp/day and 10gp/day, depending on the tier, with the option to use Monastery Incense at 50gp/day.
 
So let’s look at an example:
 
Barf the Rogue needs to learn Orc, and fast. He has an INT score of 18 so he is pretty damn smart. On my tiers, Orc needs 1500 hours to learn and skilled teacher will cost 6gp a day.
1500/18 = 84 days (we always round up) 84*6gp = 504 gp
But Barf needs this knowledge faster than that so he wants to half the time by studying under the influence of Monastery Incense 50gp/day.
84/2 =42 days. 42*56 = 2352 GP.
So Barf can learn Orc for 504 GP or in half the time for 2352.
Weapon Proficiencies work almost the same way, except that each weapon is an individual proficiency and two ability stats are combined and then divided into the required hours. For instance proficiency with a glaive for the Monk I mentioned earlier would work like this:
 
Glaive is a STR weapon so Tarbis the monk adds his STR+INT and divides that into 2500 hours (my tier level).
His strength is high (17) but his intelligence is a little above average (13)
2500/30 = 84 days. My tier for glaive runs 8gp a day so the monk is out 672 gp
I also include musical instruments, skills, and light armor proficiencies in my Variant Training. Skills and Armor Proficiencies occupy the highest tier which makes them expensive and longer to obtain. They are not considered fluff and impact the game more than weapons, languages, and instruments.
 
Please remember that while I will provide my personal tier list, you as a DM are free to create your own and rank them as you see fit. If elves are rare in your world, consider making their language higher tier because of its rarity.
 
Also remember, there is no rule stating that all this training must be completed at one time. If a player has two weeks downtime, let them add those weeks to training a new weapon proficiency or skill. When they have successfully completed the required days, let them bring in the new ability at full proficiency.
 
One the Job Training:
 
Another training variant I allow and my players enjoy is the choice to train for weapon proficiencies while adventuring. If a player uses a non-proficient weapon solely for 3 level advancements, they become proficient with that weapon.
 
Here are my tier lists for this house rule and a training sheet so players can track their advancement towards proficiency.
 
Businesses
 
Here's how we'll do it:
1 roll for every week of training
The DC = the Current ASI score of the skill you're trying to improve
Each Success = 1 tally
To improve your ASI score by 1 you need to get a number of tallys = Current ASI Score + 1
 
This is a list of commonly available people for hire. They are not loyal to you, specifically, and can abandon you if the threat (and chance of them spending their paycheck) is great enough. For those who are willing to follow you into the maws of death itself, you’re talking about Followers, characters that are as unique as they come for why they see you as the greatest thing in the world. For everyone else, coin is enough to earn their labour… for now.
 

Unskilled

The bottom-dollar store of hirelings, they have no skills or proficiencies and are just barely capable enough to sell their particular forms of labour. They’re usually plentiful thanks to the barbarity of medieval economics and desperate enough for pay to deal with all your bullshit.
 
Labourer (1cp per day): The labourer is the backbone of most functional village or city economies. From stevedores, builders, miners, chamberlains, ditchers, and scullions. They have no real ability and above-average in a single attribute, usually physical.


Conscript (5cp per day): A more intensive set of jobs than the labourer, that usually require downtime or the start of proficiency. Sailors, Man-at-arms, constables, cooks, cobblers, gardeners, or spinsters. They are usually part of a group or unit to churn out an economic practice, and thus go from job to job but still valued more than labourers.


Apprentice (1sp per day): The start of the skillful, these are usually aimed at the start of intellectual vocations and already have some basic proficiencies. Bakers, Bottlers, Clerks, Guards, Messengers, Minstrels, Scribes, and Squires.
 

Journeymen

Competent people that have become independent in their field, but aren’t established in their own business. Most artisans finish their apprenticeship or training with little to no captial, so they need to save up a nest-egg to then turn into their business. This means there is a window of time where you, as an adventurer, can trade coin for top-level skills normally requiring expensive commissions to a short-contract living wage. There is also plenty of competition for this though, so be careful about your terms or you’ll be noncompetitive with the local nobility or rival adventurers.
 
Artisan (10gp per week): The classical tradespeople, in the great tool proficiencies they’ve been certified as journeyman status and must now pay their guild to practice within the city. This includes but not limited to; Blacksmiths, Carpenters, Chefs, Herbalists, Leatherworkers, Moneylenders, Tailors, and Watchmen.


Herald (15gp per week): For the more dramatic and leadership based vocations, they are usually excellent at managing people in every facet. Includes but not limited to; Actors, Butlers, Singers, Ship Captains, Performers, Reeves, and Winemakers.


Librarian (25gp per week): For those with excellent intellect and training but no agency or capital for their own projects yet. Includes but not limited to; Apothecary, Astrologist, Enchanters, Engineers, Sheriffs, Shipwrights, and Researchers.
 

Mercenary

Masters of their various fields, with excellent proficiency, skill and raw ability. Hiring these individuals is more a mutual contract and they usually require impressing before they will hire on for even a short contract. Their opinion and well-being is worth considering, at very least just because of their cost. They can afford to not work for quite a while.
 
Myrmidon (150gp per month): Named for the famous Dragonborn Myrmidons of Myrmyr, who hire out themselves for personal bodyguarding and wetwork. They are usually brutal and antisocial individuals whom violence comes quickly and protect their charge well. They include but are not limited to; Mercenaries, Myrmidons, Ronins, Spellswords, Warlords.


Valet (3,000gp per year): A personal assistant for your convenience, they are a mark of station for most nobility and for any long-term blend into high society requires one. They are extremely skilled and dedicated to their craft. They go my many titles but mostly fill the same function; Bates-man, Chaplain, Chancellor, Marshall, Porter, or Steward. Their role can be as expansive or narrow as you deem, but they usually expect board and food as standard with their stipend.


Doctorate (6,000gp per year): Someone of great renown or ability whom has surprisingly sworn to work for you. They are usually great commissions, and include such things as; Arcanists, Doctors, Inventors, Painter, Planeswalkers, Sculptors, Spiritualists and Ranger-Lords.
 

Animals

A collection of commonly trained and traded beasts for adventuring lifestyles.
 

Guard Dog (25gp): A massive wolf-hound trained to protect you and track creatures via scent.
 
Hound (small)
AC: 13 (Barding Costs similar to Humanoid) Hit Points: Level x6 Speed: 40ft
Str 13 (+1) Dex 14 (+2) Con 12 (+1) Int 3 (-4) Wis 12 (+1) Cha 7 (-2)
Saving Throws: Str +Proficiency Bonus, Dex +Proficiency Bonus, Con +Proficiency Bonus
Skills: Perception +3 (Advantage to Hearing and Smell)
Pack Tactics: The hound has advantage on an attack roll against a creature if at least one of the hound’s allies is within 5 ft. of the creature and the ally isn’t Incapacitated.
Bite: +2 +Proficiency Bonus to hit, 1d6 +1 +Proficiency Bonus piercing damage. If the target is a creature, it must succeed on a DC 10 +Proficiency Bonus Strength saving throw or be knocked Prone.
 

Steppe Pony (30gp): The hardy ponies of the dwarves people, as strong as a full sized horse and twice as hardy, but their shorter legs do reduce their run speed slightly. Bridled and saddled with moderate equipment packs.
 
Pony (medium)
AC: 10 (Barding Costs similar to Humanoid) Hit Points: Level x6 Speed: 40 ft
Str 15 (+2) Dex 10 (+0) Con 13 (+1) Int 2 (-4) Wis 11 (+0) Cha 7 (-2)
Saving Throws: Str +Proficiency Bonus, Dex +Proficiency Bonus, Con +Proficiency Bonus
Powerful Build: You count as one size larger when determining your carrying capacity and the weight you can push, drag, or lift.
Hooves: +2 +Proficiency Bonus to hit, 1d4 +1 +Proficiency Bonus bludgeoning damage.
 

Hunting Bird (50gp): A difficult prospect in training, but an incredible asset for hunters, trackers, and guardians of the woodlands.
 
Falcon (small)
AC: 13 (Barding Costs 1/4 Humanoid costs) Hit Points: Level x 3 Speed: 10ft, Fly 60ft Darkvision 60ft
Str 6 (-2) Dex 16 (+3) Con 13 (+1) Int 8 (-1) Wis 14 (+2) Cha 11 (+0)
Saving Throws: Str +Proficiency Bonus, Dex +Proficiency Bonus, Cha +Proficiency Bonus
Skills: Perception +2 +Proficiency Bonus
Flyby: The beast doesn’t provoke opportunity attacks when it flies out of an enemy’s reach.
Shred: +3 +Proficiency Bonus to hit, 1d6 +3 +Proficiency Bonus slashing damage.