When do you NOT care about money?

I think you nailed it. It is really not a question of price, but of value. There are always "cheaper" options and there are always luxury options for almost every purchase but the sweet spot is finding that value.

If I think about it, I don't really question the "price" of items anymore, I question the "value."

And obviously, that is very subjective. So back to the example of the $7.99 giant cookie... it isn't automatically too much to pay if it is the best cookie you've ever had. What makes me mad is when you buy something like that and it turns out to be just disappointingly average (or even bad). That bothers me much more than the price.

Most people don’t have 1 to 1 utility functions for $.

the answer to your question is: when they lower you into the coffin

I spend extra money to buy convenience.

Another situation is when I am not sure if I will ever get something similar at a lower price. I want to eliminate the element of uncertainty by spending more money.

I also spend extra when I want the seller of goods or service to make more money. Then I feel good about spending extra money to make someone else's life better.

I still care about what I spend, but I don’t agonize over it.

I’ll spend a bit extra for quality clothing like Vuori or Lululemon, but would never spend $600 on a Gucci T shirt.

I’m going to Japan next month and excited to stay at a couple nice places, which will cost about $7K just for lodging over 2 weeks (for a family of 5). I could easily spend 5-10 times that much with suites at the Ritz or Mandarin Oriental. We’re also flying coach and saving about $4K over premium economy as I can get through 16 hours of a little less comfort for 2 weeks of very comfortable accommodations.

Yes. That is a good example. I like to strike that balance... I'll put up with flying coach (family of 5) but then we have a much nicer vacation once we land. Stuff like that.

Honestly, the things that bother me the most are when by trying to save money, I end up wasting time. Or when I do spend more for something and the product is totally average. Those two scenarios bother me the most.

I like to treat my friends to a good time. A few times Ive picked up the tab for a large group after an evening drinking, eating, etc.. fun times. It was worth every penny. I never thought about how I wished that money was in a mutual fund or whatever.

That is another good example. There is tons of value in that. I have no problem picking up the tab. It feels more "worth it" to spend $100 for the whole group than to spend $30 on myself.

The other side of the coin happened on Friday when I was on my way to my kid's track meet. I was a early so I stopped and ordered two tacos and some chips & salsa. It ended up being like $25 and none of it was particularly good. I wish I could have had those $25 back (and the calories).

Hookers ...