I was frustrated by how same-y, illogical, or poorly-worded (or all three) all the generators I found online were. Let’s use an example result generated from the Barrel, Crate, and Sack Generator from Wizards of the Coast for D&D:

• Sacks (Medium 1d6)
  • Medium Sack: 800oz, 50pt, 50lb
    • Sack (16): Lovage (Spice/Seasoning) 1sp per oz (80gp)
    • Sack (15): Olidammara’s Dice — Epic Level Handbook (Magic Items).
• Crates (Medium 1d6)
  • Medium Crate: 27cu.ft, 3232oz, 202pt, 202lb
    • Crate (9): 2d6 Goods (Clothing) from PHB Table 7-8
    • Crate (8): Copper (Precious Metals) 5sp per lb (101gp)
    • Crate (7): Barley (Flour) 2gp per lb (404gp)
    • Crate (6): Alchemical materials, unusual (Commodities) 50sp per oz (16,160gp)
• Barrels (Medium 1d6)
  • Medium Barrel: 32gal, 4168oz, 256pt, 256lb
    • Barrel (11): Lentils (Corn) 2gp per lb (512gp)
    • Barrel (10): A magic item from DMG Table 7-1 or see Magic Item Compendium Appendix 2 (Magic Items)
    • Barrel (8): 2d4 Goods (Adventuring Gear) from PHB Table 7-8
    • Barrel (7): 2d4 Goods (Tools and Skill Kits) from PHB Table 7-8

Leaving aside the fact that the player characters are apparently carrying around an industrial scale capable of measuring 4,168-ounce barrels with such exacting accuracy, this generator suffers from over-complexity and under-specificity at the same time.

Sack of lovage? Okay cool. How much lovage? Now you gotta do reverse math because the total container weight listed is the aggregate of all the same style of containers. At 1sp per oz and it’s worth 80gp total, 80gp = 800sp = 800 ounces or 50 pounds of loveage. Do you or your players really need to know the unit price? If the PCs even bother picking it up, they’re gonna unload it at the nearest town and the only numbers they care about are 80 gp and and 50 pounds for encumbrance reasons. Just say 50 lbs of loveage worth 80gp and if you have a player insisting on doling it out by the ounce like some sort of medieval weed dealer, make them do the math.

Moving on to the medium crate which contains Alchemical materials, unusual (Commodities) 50sp per oz (16,160gp), meaning there’s 202 pounds of alchemical materials. Great, that’s an awesome haul for the party’s alchemist. But what are the alchemical materials? Rare creature parts, solid gold cauldron stirring sticks, bottled phoenix farts, what? This kind of entry just lacks imagination and creates more work for the GM.

Shameless generator pimp: Magical Ingredients

Moving on to the barrels. We have 4 barrels containing an absolute crap-load of lentils, a magic item, 2d4 goods, and 2d4 goods. Really, WotC? Now we gotta go hunting through the PHB/DMG and roll yet more dice, and five minutes later finally get around to telling your players that they found yet another Mirror, small, steel and hang on while I generate good #2…

If you hit the generate button some more to get different contents, you begin to see the problem: repetitiveness. All of the results generated are a variant of:

• 𝑥 pound sack of random herb, vegetable, or fruit
• 𝑥d6 goods of type 𝑦 that you have to generate yourself
• random armor, weapon, potion, or magic item that you have to generate yourself
• a ridiculously overpowered magic item, if it’s not an artifact
• a jewel, piece of jewelry, or art object from the very small list of gems and art objects

There’s no imagination. Eventually your players are going to run out of the listed art objects and you’ll be fumbling to come up with a description for a piece of jewelry worth 230 gp. This is where a generator would really come in handy. Let’s find such a generator! Here’s some examples from Chaotic Shiny’s Art Object Generator.

A very large oil painting of a sparrow and a helmet. The predominant color is vibrant blue. The frame is made of silver.

Ah now, that’s much better.

A small steel statue depicting a relationship ending involving a short, squat assassin.

Hmm, that gives me an adventure idea…

A very small mosaic of a treasure chest and a lynx. It is in good condition.

Good variety! Giving the condition is a good indicator of whether the players might get max value for the item or not.

A somewhat large cedar sculpture of an amethyst.

Er, okay. Hey, it’s art, critics abound.

A small wall painting of an old woman and an old woman in abandoned ruins. The frame is made of silver.

Another painting, apparently of a female Janus, also framed in silver. Okay, fine, I can forgive this one; the RNG gods just played the odds very well.

A small oil painting depicting a financial difficulty involving a short, clever spy at twilight. It is in poor condition.

Now here’s where it gets ridiculous.

My point being, Chaotic Shiny’s art object generator is a vast improvement on WotC’s boring short list. Why? Chaotic Shiny has a much, much larger vocabulary list and more than one syntax.