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The Dungeon Master's Guide on page 127 lists the costs of maintaining various buildings. While some of these make sense, of note is that Shops and Trading posts are listed. This means that, rather than being a source of money, these actually cost the player money to own. Below, under "Total Cost per Day" it says that the cost is indeed the net income of the property, after sales.

I'm struggling to understand why a shop or trading post would be unprofitable by default, or why a player would want to own one in that case.

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You're only getting half of the information. After the table, the blurb on Businesses (same page, DMG 127, right below the table you've cited) explains that the information for running a business is in the section for Downtime Activities (which also starts on that same page).

The relevant section in Downtime Activities is on page 129 of the DMG and is titled Running a Business. This section includes die tables for how successful your business was while it was open (ex: On a roll of 41-60 "Your business covers its own maintenance cost for each of the days"), and information on selling specific magical items (like how many days it takes to find a buyer depending on rarity, and the percentage of the value a customer is willing to pay).

So it can be quite lucrative to own a shop, actually.

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You must work in your downtime if you want to make profits.

The "total cost per day" value in the table assumes the character does not attend to the business. So if you ignore your business altogether it will cost you money. If you want to make profit, you must run it at least in your downtime. It is explained in the Running a Business section on page 129. If you spend time in your downtime activity you roll 1d100 and add the number of workdays you spend doing business and you can make profit if you roll high.

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Yes owning a business cost money. It's also true in D&D

Unless you have slaves, never feed them, live in a land without taxes and don't produce anything, a business will cost money. Cutting wood from trees and making chairs might seem like a cheap activity but you need tools, room to store wood. Eventually tools break and you need to replace or repair them. The cost increase depending on the business. Managing a tavern (imagine the cost of all those adventurers breaking stuff and starting brawls) will be more expensive than being a flute maker. You also need customers to buy from you and it can be difficult to convince people to buy from you instead of someone else (specially in a world where bargaining is expected for every transaction).

Instead of overcomplicating the process by going into specifics the DMG set a base cost based on the type of business. The base cost covers everything (tools, land, taxes, possible lost/stolen items, salary of skilled and untrained employees etc.) and then you, the business owner walks in.

Unless your business is established and so big and using a really modern infrastructure, you can't just go on carousing every night like Tony Stark and let the NPC employees manage the business. Why? Because when the boss is not around it gets messy. When the owner of a small business is in the tavern drinking and playing dice and the entire town knows about it, it could hurt the business reputation and people don't go to a business where the manager is obviously too busy. Coming from a small town myself, people create relationship with business owners and if the owner is never around, they usually gravitate to a business with a more caring or charismatic owner. Employees become lazy (or outright steal from you) when the boss is not around.

So based on the rules, which abstract a lot for you, if you own a large business and spend a lot of time there (during your downtime) you'll get bonuses to roll for a probable profit. Unless you neglect the business or you are incredibly unlucky, you'll make money. In the end, it can be really lucrative to own a business. It's also a lot of fun and can bring a lot of roleplay and even adventures to the game.

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    \$\begingroup\$ I don't think the real question was "does a business have costs?", but was instead "why does it look like businesses always have a net loss?" which is very different. \$\endgroup\$ – Mooing Duck Mar 20 '15 at 17:57
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The prices of shops and trading posts represent the basic cost of doing business. Income from the business is handled separately. Ideally, income from the business is supposed to make up for this cost, and then some: once your costs are paid, anything left over is your profit. If you don't bring in enough business, then you lose money.

As far as businesses work, this is a fairly simplistic model, but it's accurate enough as far as it goes. Real-world businesses incur costs, which they try to pay for using the money they get by doing business. When they make enough money to do this, great. When they don't, they're in trouble.

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The system has a way in the book to gain profit that negate some or all of the costs, it has a flat gain (I think for simplicity) but at the cost of making all potential gains equal regardless of the initial cost or the risk of losing money/having to pay the upkeep. Cheaper to maintain businesses become strictly better than more expensive business, so the real question becomes why would a rational individual run a business like a trading post when they could run a small farm?

I would recommend following the base guidelines in the DMG when it comes to the days worked and profit rolls for business and tweak the results that actually earn money to have some scaling based on the expected cost — unless you're just satisfied with the potential of making profit and not costing, then just keep it the way it is. The average profit should range between 7.4 gp - .45 Maintenance cost and 12.35 - .05 Maintenance cost, which would result in anything with a maintenance cost of 148 gp or less being on average profitable and businesses with a maintenance cost of 148 gp or less unprofitable even if one works all month, and if one works the bare minimum, one could only make a profit on average from a business that costs less than 16.44 gp. The multiplier I would recommend would be between 5% and 30% (but definitely not at 30%), as that would be the average gp value to be able to make up the maintenance cost on average, with a bonus of the gp on the table, even though the percentage could replace it. What percentage would depend on how much you want to encourage PCs in a business and how long you think they will work on it every month.

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