A lot of these seem like someone read an article about travel in medieval Europe traditions of hospitality and then used wording that make it sound like "must" instead of "typically". Traditionally, if someone was going on pilgrimage they didn't stay at taverns or hotels, they stayed with individuals along the way.
In any case I view all of these as suggestions. Things I'll try to take into consideration but also probably the least important when it comes to who the PC is. The main issue is that some are quite powerful from an in-world point of view while others are so minimal as to not matter.
Acolyte: You and your adventuring companions can expect to receive free healing and care at a temple, shrine, or other established presence of your faith, though you must provide any material components needed for spells.
Free healing? Depending on campaign this is a pretty big benefit or a big nothing. I don't have many temples dedicated to a specific deity and in the majority of places where my campaign takes place most temples could be considered of the same "faith" since human and non-human pantheons are linked. In other words, Moradin supports the Aesir by crafting weapons etc..
Charlatan: You have created a second identity that includes documentation, established acquaintances, and disguises that allow you to assume that persona.
This assumes you know what the documentation would look like. If you do, that's fine. Acquaintances? Where? How many? What purpose do they serve? Do you have to have proficiency in a disguise kit and how good is the disguise?
This is an okay starting point, just a lot is left up in the air.
Criminal: You have a reliable and trustworthy contact who acts as your liaison to a network of other criminals. You know how to get messages to and from your contact, even over great distances; specifically, you know the local messengers, corrupt caravan masters, and seedy sailors who can deliver messages for you.
Having a contact is fine. We'll work something out on who the contact is, how the PC knows them, etc. They become a valuable NPC with a name and personality, along with the goals and desires. However, it's just one contact to one criminal organization. There are going to be limits and I'm not going to guarantee safety.
It also implies that this one contact can get you in touch with any other criminal in existence which makes no sense. The whole getting and sending messages over great distances is always going to be up to the DM. It really doesn't make sense that we can get messages back in forth under some circumstances.
Entertainer: You can always find a place to perform, usually in an inn or tavern but possibly with a circus, at a theater, or even in a noble's court. At such a place, you receive free lodging and food of a modest or comfortable standard (depending on the quality of the establishment), as long as you perform each night. In addition, your performance makes you something of a local figure. When strangers recognize you in a town where you have performed, they typically take a liking to you.
How famous an entertainer? What's the origin story and age of the PC? If someone says they're 20 and they've entertained kings, it's a stretch. It's also "even in a noble's court" not something that's guaranteed.
Details, like how long you get free lodging is open to interpretation.
Folk Hero: Since you come from the ranks of the common folk, you fit in among them with ease. You can find a place to hide, rest, or recuperate among other commoners, unless you have shown yourself to be a danger to them. They will shield you from the law or anyone else searching for you, though they will not risk their lives for you.
I'm okay with this one, but the "will not risk their lives for you" is another vague thing. Are they "risking their lives" if being caught means they become an indentured servant, lose all their property, have to pay exorbitant fines that will destroy their lives as they know it or is it just capital punishment?
Also, what happens when the local boy done good becomes wealthy and famous? What if they become infamous because of the crimes they are accused of? Can the those "common folk" (I kind of hate that term) turn against you? For that matter if you're a folk hero because you managed to somehow get a warning out on a midnight ride that the Drits were coming, how much hospitality do you get if you're in Dritain and the commoners should all hate you?
Guild Artisan:
As an established and respected member of a guild, you can rely on certain benefits that membership provides. Your fellow guild members will provide you with lodging and food if necessary, and pay for your funeral if needed. In some cities and towns, a guildhall offers a central place to meet other members of your profession, which can be a good place to meet potential patrons, allies, or hirelings.
Guilds often wield tremendous political power. If you are accused of a crime, your guild will support you if a good case can be made for your innocence or the crime is justifiable. You can also gain access to powerful political figures through the guild, if you are a member in good standing. Such connections might require the donation of money or magic items to the guild's coffers.
You must pay dues of 5 gp per month to the guild. If you miss payments, you must make up back dues to remain in the guild's good graces.
Again, this is a local thing. Guilds didn't span the globe. Quite an odd note that they'll pay for your funeral. Also odd that they establish dues.
Hermit:
The quiet seclusion of your extended hermitage gave you access to a unique and powerful discovery. The exact nature of this revelation depends on the nature of your seclusion. It might be a great truth about the cosmos, the deities, the powerful beings of the outer planes, or the forces of nature. It could be a site that no one else has ever seen. You might have uncovered a fact that has long been forgotten, or unearthed some relic of the past that could rewrite history. It might be information that would be damaging to the people who or consigned you to exile, and hence the reason for your return to society.
Work with your DM to determine the details of your discovery and its impact on the campaign.
This is an okay starting point but can be tough for a DM. Any discovery that makes a huge difference to impact the campaign is establishing a campaign direction. This can be a good thing for some, incredibly difficult for others. In my campaign the direction the party takes is very dependent on what the players want to pursue, I may have a problem coming up with this because my view of things outside of the near future sessions can vary wildly.
Noble: Thanks to your noble birth, people are inclined to think the best of you. You are welcome in high society, and people assume you have the right to be wherever you are. The common folk make every effort to accommodate you and avoid your displeasure, and other people of high birth treat you as a member of the same social sphere. You can secure an audience with a local noble if you need to.
This horse is dead.
Outlander: You have an excellent memory for maps and geography, and you can always recall the general layout of terrain, settlements, and other features around you. In addition, you can find food and fresh water for yourself and up to five other people each day, provided that the land offers berries, small game, water, and so forth.
One of those that makes sense but is also covered by other proficiencies and class abilities. Not bad, just not particularly important.
Sage: When you attempt to learn or recall a piece of lore, if you do not know that information, you often know where and from whom you can obtain it. Usually, this information comes from a library, scriptorium, university, or a sage or other learned person or creature. Your DM might rule that the knowledge you seek is secreted away in an almost inaccessible place, or that it simply cannot be found. Unearthing the deepest secrets of the multiverse can require an adventure or even a whole campaign.
Situationally beneficial but I don't care if you were the head librarian in Candlekeep, if you're in Avernus it's not going to help much. My current PC is in Ravenloft, accessing a library for info would make no sense in this campaign.
Sailor: When you need to, you can secure free passage on a sailing ship for yourself and your adventuring companions. You might sail on the ship you served on, or another ship you have good relations with (perhaps one captained by a former crewmate). Because you're calling in a favor, you can't be certain of a schedule or route that will meet your every need. Your DM will determine how long it takes to get where you need to go. In return for your free passage, you and your companions are expected to assist the crew during the voyage.
Again, based on connections. I'll give someone a huge benefit of the doubt in a foreign port but it's not a guarantee.
Soldier: You have a military rank from your career as a soldier. Soldiers loyal to your former military organization still recognize your authority and influence, and they defer to you if they are of a lower rank. You can invoke your rank to exert influence over other soldiers and requisition simple equipment or horses for temporary use. You can also usually gain access to friendly military encampments and fortresses where your rank is recognized.
Another one that it just depends on "where your rank is recognized". If you're in Dritain and your rank is from those darn rebellion states I doubt you want to be recognized. It does make sense, but "defer to you if they are lower rank"? Respect, yes. Advantage and/or lower DC on a lot of social checks? Sure. But just because you were once a captain, it doesn't mean a private is automatically going to risk court-martial for disobeying their current chain of command.
Urchin: You know the secret patterns and flow to cities and can find passages through the urban sprawl that others would miss. When you are not in combat, you (and companions you lead) can travel between any two locations in the city twice as fast as your speed would normally allow.
The feature is general enough that it makes sense in most cases. It rarely matters though.
In the blue corner, we have a jiu jitsu fighter with words. Able to tap people out with semantic choke holds. How will they choke out their opponents?
And in the red corner, we have a muay thai fighter with words. Able to knock people out with their clever punches. How will they knock their opponents out?
I mean, seriously read these things. The interpretation scale (at least in my opinion) is off the charts.
But all fighting puns aside, I am curious to see how the logic we've been applying to the noble feature applies to others.
Any and all features have to make sense in context for me. The actual feature paragraph isn't the only thing I take into consideration and I often give people benefits that aren't based on the text there. Backgrounds are starting points for me.
If it's important to the player I'll do my best to make it beneficial but it won't override my world building. If I say no or modify a feature it's not because I'm trying to "thwart" anything. If there's a goal there will typically be multiple ways of achieving it (including options I don't think of), a background feature may just not be one of those. But if it does apply? Even if it means they bypass what I thought was going to be a major obstacle? Cool. Happens all the time for all sorts of reasons. That is not why I will say a feature isn't applicable.
