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By level 49, I have collected hundreds upon hundreds of various items during my quest. I have accumulated so much loot, in fact, that I need to use 6 barrels in Riverwood to categorize my wide assortment of stash, each one heaping full with armor, weapons, gems, jewelry, potions, ingredients, ore, ingots, magic books, scrolls, and other miscellaneous items that carry a good sell value. If I were to follow through with my plan and sell off everything I have, I'd easily walk away with 50k+ in gold. There's just one small problem...

...no merchant is rich enough for my patronage =\.

In fact, I don't think all the merchants in all of Skyrim combined are rich enough.

I know there are perks I can get that allow me to sell a wider range of items to vendors that would be otherwise uninterested and perks that will put more gold in the vendors' pockets, but no perk will give me the edge I need to completely liquidate my inventory.

What is one to do? Simply stop collecting loot since no one in Skyrim can afford to buy it?

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You people do know that Oblivions Shivering Isles expansion had a quest where you had to gather 50 calipers and 50 tongs? Finally all the hoarding paid off –  Ids Jul 6 '12 at 19:11
    
if you're really motivated to move your junk, just keep fast-travelling across the country, your merchants gold supply will restock every so often. –  Michael Edenfield Aug 27 '13 at 18:18
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I sell as I loot. The merchants seem to get more cash every day or so. So if I have a big haul I sell what I can and I keep a special chest just for stuff I know I want to sell. So if I have a day in town I do nothing but hang out at the pub drinking, or spend crafting or something, I go back to that chest and sell more the next day.

Plus you can trade instead of sell, buy soul gems or alchemy ingredients or such that will always be useful.

Of course at nine barrels of loot you are way behind. Fast travel to vendors in each city?

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This is definitely what I wish I had done, sold as I go, and probably the only solution to my issue. Another issue, though, is that I like to hoard weapons and improve/enchant them in bulk later. I really wish merchants would carry more gold. –  oscilatingcretin Jun 16 '12 at 0:38
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Well, if you are playing on Windows you can find some mods in the Steam Workshop for Skyrim that enhance merchants so they may have more money. One I saw browsing quickly is called Dynamic Merchants. It isn't a blantant cheat either, the rationale is that the more you deal with a merchant, the more successful and prosperous they are, so they more money they will get. –  PhysicalEd Jun 16 '12 at 18:24
    
If I'm not mistaken, the "every day or so" is approximately two days. Usually if you make a full tour of all the shops in skyrim, you will have run out the refresh timer by the time you get back to the first one. If not, just wait two days and go again. –  Iszi Feb 15 '13 at 6:10
    
Even the tour of Skyrim does not work sometimes. The value of my enchants is sometimes more than 5000 Septims. No merchant has that kind of gold, unless its the Riverwood trader unpatched with 11000+ septims. –  ヴァイシャリ Feb 11 at 17:07
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fellow Skyrim hoarder!

First, you want to move all that stuff to your own house in Whiterun. The barrels are not guaranteed safe in the long term. There are numerous chests and other storage items, including bookshelves, end tables and sacks.

You can gradually liquidate your stock by selling little at a time, and fast travelling between towns to sell your junk. Shops eventually recover their gold, so sell a little of your junk every time you visit the city. Buy everything you can first, because that'll increase the seller's current money, so you can sell more things.

Another trick is that some shopkeepers (such as the alchemist shop in Whiterun) also give skill training. Money you spend on training goes into the seller's current funds, which lets you sell a lot more.

Some stuff is useful, so it's worth hoarding. Alchemical items can be used to craft hundreds of potions in one go and max out Alchemy. All those ancient Nord swords can be enchanted in one sitting to raise Enchanting, ingots to make weapons, and so forth.

Stop picking up truly useless items, though. Especially ignore junk with a high weight to value ratio and no use, like embalming tools and tankards.

When you're high level and have a lot of gold, you'll run out of things to spend it on. At this point, stop bothering with low-end items like steel or orcish swords. Ignore anything unless it's useful or worth a lot.

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Money you spend on training goes into the seller's current funds Best advice ever. I was not aware of it. Thanks. –  ヴァイシャリ Feb 15 at 7:08
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Money is not in issue in Skyrim, merchant gold will likely be the limiting factor in how much loot you can move. Cherry-pick what you take home, only take things that are genuinely useful.

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But I love getting Nord and Foresaken arrows. They rule. It is so awesome when I run out of other much better arrows in the middle of a dragon fight and it selects something way down the list. –  Wayne Arthurton Jun 15 '12 at 1:50
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I have found that the thieves guild is the best place to sell you loot. Even when you just join there is a fence, who buys anything, and has a thousand gold. If you go through the quest line and upgrade the guild, there will be merchants with thousands of gold to buy loot.

Their money supplies will refresh every few days, so you can just go back and keep selling.

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This is what I ended up doing in my third (and final) play-through. I load up on stock from my barrels in Riverwood, sell to Alvor, sell to that other guy with the claw, fast travel to Whiterun to sell to that smith, then fast travel to Riften to sell to Grelka, that smith guy, and then save my stolen or non-stolen leftovers to Tonilia. Works great. –  oscilatingcretin Jul 6 '12 at 19:03
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Also, with Grelka, you can max out on light armor training and then sell her more, so you're basically trading skills for weapons and armor. –  oscilatingcretin Jul 6 '12 at 19:04
    
@oscilatingcretin I never thought of that. Thanks. –  ヴァイシャリ Feb 15 at 7:04
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Sell as you go. Always keep what you can carry. Hoarding is pointless in Skyrim. The most gold that you can count on a frequent merchant is *2500 , so don't let it break your mage-heart to sell each of those anchanted swords, bows and heavy armor that are worth 5-10k each for only 1k ... because the items are useless. Instead of trying to make money, make the challenge for you to have the most room to pick up the better loot at the next location.

This brings me to merchants. Invest. Don't just sell to them. Buy what you need and sell again to get your money back. At lvl63 (99-legendary Speech) it's tough to have less than 50k gold with me.

If you like the feature of selling items for currency, raise your Speech. The more often you barter, the faster the skill raises. Same as all other skills.

I postulate that most things reset upon leveling up. Playing on higher difficulty is the most rewarding. If you have your top 10 (or 5) places to loot, odds are that once you sell stock that first cave is going to be ready again with better loot.

If you're keeping a spare parts pile at home for enchanting... that's the only reason to keep anything. Always disenchant before selling.

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Honestly I would not loot as much. I generally only loot gold now, because i have a plethora of weapons and armor as well. The only items i generally collect are the daedrict artifacts because they took a while to get all of them. But if collecting loot is your thing, then go for it, just don't look to be able to move it all very well.

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No it's not worth hoarding all that stuff. Once you get the merchant perk in speech and can sell any non-stolen item to any merchant it becomes easy to make money. Potions can be made and sold to anyone. An iron dagger with the banish enchanment fetches me thousands at any merchant and I can make it for about 40 septims.

Learn soul trap, learn some enchantments, smith iron daggers, enchant said daggers, profit.

Now, I just make sure to carry around 10 enchanted daggers when I go adventuring. I loot everything I want, or the most expensive sellable stuff, then when my inventory is full I go back to Whiterun. I have 4 merchants right by my house to unload that gear onto. I buy all the raw materials they have (as well as any weapons/armor with new enchantments), then I sell my junk/potions/enchanted daggers until they are broke. Move to the next merchant repeat. Every time I go to Whiterun I clear out 4 merchants of raw materials and gold, then go to my house to dump all the raw materials.

At some point I am going to legendary my smithing, load up 8,000 lbs worth of smithing supplies, slowly walk next door to the forge, and get my smithing back up to 100 in one session.

I have about 75k gold right now. Not sure what to do with it. Eventually I will be buying all the houses and upgrading, but as of now I am making money faster than I know what to do with it. Especially since I can invest with most merchants. I instantly get my 500 investment back by selling them enchanted gear, and I get that extra 500 every time I come back too.

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If you get the perk which allows you to sell any kind of item to any merchant, then you can go round selling to all the stall owners in riften, which is just quicker because they're outside, then save all stolen goods for tonillia. :)

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If you read the question closely, the asker is aware of the Merchant perk, but this isn't solving the problem. –  Coronus Mar 5 '13 at 0:16
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