Sean always starts with $3.20

Esteban(dad) = lying will get you $20 while telling the truth gets you $40

"Drug" Money Jar = either gain -or- lose $10 (this one time, it doesn't count as stealing)

Diner Receipt = always lose $12.90

Bear Mart:

• Power Bear = the bear ;) minimum seems to be $3 by having the same character try 3x; even if the graphics show you snagging a sphere before the 3rd attempt, the game will not give it to you
  
• Choco-Crisp = steal, lose $2, or break your promise
  
• Tent and Raccoon Sweater - too expensive to buy; either steal or go without. You get both if you choose "Steal Camping Gear" later on
  
• Sleeping Bag = too big to steal; lose $16 or go without
  
• T-Shirt = too big to steal; lose $11.90 or go without
  
• Food = you need 2x of the following to make sure Daniel has enough to eat; Hot Dogs ($6) Bread ($5.90) Mac & Cheese ($4.50) Chips (free w/ begging) so without stealing you'd have to pay a minimum of $4.50, steal, or not get Daniel enough to eat (apparently no one eats the dumpster apple and candy doesn't count)
  
• Drinks = there doesn't seem to be any reason NOT to just drink the free tap water

Nothing consumable will carry over after this meal so there is no reason to stock up on extra food/drink

Brody = always gain $30

Vending Machine = always lose $1

Sean starts with a minimum of $4.03 up to a max of $30.03

Christmas Market:

• Wreath = $10
  
• Sitting Bear = $6 -or- $7
  
• Snowman = $4 -or- $5
  
• Wooden Beaver = $9 -or- $10

You get the discounted price if you are honest (and reveal your identity) to the guy behind the counter
You can steal the Yo-yo and then replace it with a bought item or give Daniel multiple presents

Cassidy = lose up to $1 (if you have less than $1, you'll give her your last 3 cents)

Everyone seems to have $1421.31 at the start of this chapter regardless of how much money they had left at the end of chapter 2. That means there is no reason not to spend your cash in the previous chapters

Furthermore, this appears to be the case from this point on; how much money you have in each chapter is simply hard coded going forward.

If I missed anything or got anything wrong feel free to let me know in the comments!