All data here was collected from my own runs, I didn't actually know there were other guides with the same information until I made this one. That said, I did see an error in the other Big Jeremy request list guide, and the other item value guide didn't have the item rarities included (they don't mean much, but it's still extra info). I don't know how to format a guide though, so no fancy colored text or anything, sorry :(

- Common (Gray) -
3 TP : Boot
3 TP : Can
4 TP : Rubber duck
4 TP : Soap bar
4 TP : Wrench
5 TP : Lighter

- Uncommon (Green) -
5 TP : Canteen
6 TP : Old coins
6 TP : Padlock
7 TP : Flashlight
8 TP : Watch
9 TP : Flare gun
10 TP : Binoculars
10 TP : Candlestick
$1 : Bronze coin

- Rare (Blue) -
12 TP : Goblet
13 TP : Golden plate
14 TP : Silver ring
$2 : Silver coin

- Epic (Magenta) -
15 TP : Brozne statue
16 TP : Golden ring
16 TP : Silver Idol
18 TP : Skull ring
$3 : Gold Coin

- Legendary (Yellow) -
18 TP : Silver statue
20 TP : Golden statue
23 TP : Golden Idol

- Mythic (Red) -
30 TP : Gold bar

Soap bar for $5
Lighter for $7
Wrench for $10
Canteen for $12
Watch for $15
Candlestick for $18
Goblet for $20
Brozne statue for $23
Silver Idol for $25
Silver ring for $28
Golden plate for $30
Golden ring for $35
Skull ring for $40
Gold bar $50

For fun, I mined out the entire hole and put every single item that was reachable on the table, just to see how much it would all sell for at once. This value will vary, of course, as well as the number of items each hole contains, but it's an interesting reference point. In total, I got 376 items from the pit. (Not including bronze, silver, and gold coins, which all turn directly into money on pickup and can't be held or sold.) This is what that looks like on the selling table.

Loading the save takes me several minutes, and when the game finally unfreezes, you get to watch all of the items fly in from somewhere outside of the room and onto the table. It takes the guard several in-game hours to siphon it all into his spacious pants hole. It's quite the sight, I'll include a link for this save at the end if you want to play with it. All in all, this haul sells for 2,321 TP. Not much for an entire holes worth when the last shovel costs 5,000 TP, or 1,500 with max prison rep, huh? It sure is lucky the guards kindly refill the hole with dirt and treasure every time they catch you loitering at the slot machine trying to get one last payout before going back to your cell...

Of note, it is impossible to have more than one holes worth of treasure at once, as getting busted removes all loot both on the table and in your bag, sadly. Still, this score could definitely be beaten with better luck, but I'm not bothering to do this more than once, personally.

These places are blocked off by invisible geometry that continues off of nearby surfaces, so this dirt is undiggable and this loot is unlootable. Dev, please fix >:(

Edit: In the process of getting these screenshots, I tried to throw a flare on this wall...and it passed right through, as you can see by the glow on the floor and right wall here.

Turns out this wall is actually fake, and contains a bit of extra dirt and loot I'd missed! I'm not editing ♥♥♥♥ though, sorry, just pretend the total item count and sell value are ever so lightly higher. Not all the dirt and loot hidden behind this fake rock are accessible, much of it is stuck behind that same invisible wall in that second screencap up there, but there is a bit in here you can reach. I'm just inside the wall here, in this next image.

Sneaky.

Here's the download for the save used to get this data, complete with comically large pile of loot and thoroughly mined-out hole. The save has all items and upgrades bought, all stats maxed, all Big Jeremy quests completed, a couple thousands bucks left over from gambling, and of course the hole is completely excavated to the best of my ability (minus some spots which are blocked by wonky geometry).Just replace the "Prison Escape Simulator" folder in
C:\Users\%userprofile%\Appdata\Locallow\Digital Melody Games
with the one from the Drive. You can just open file explorer, click the empty space on the right of the bar with the file path to select it, and paste that line up there into it to see the right folder. If downloading the full thing takes too long and you don't care about the hole staying dug, you can just grab the "Save" folder from the download, the "DiggerData" folder takes longer to copy.
Save a copy of the existing folder somewhere if you don't want to lose your save, obviously.

https://drive.google.com/drive/folders/1Qplvl9sGIG5jR6awKN7O_d3UzHCuRIWf?usp=sharing