How do you manage optimizing everyday purchases?

I'm quite shocked on how hard it is to keep track of credit cards and rewards programs. I've been watching some of my friends obsess over maximizing every cent from their credit cards and loyalty programs and how much time that takes them. They use all these apps, some have spreadsheets, etc. It seems like so much work though for such a solvable problem.

I tried to pay attention to my rewards this week and every time I buy something, I spend a couple of minutes figuring out which card to use. 3% back on dining? 2x points on all purchases? What category does this shop count as? list goes on…

The absurdity hit me. We have software that can drive cars, yet we're doing mental gymnastics over pocket change. I'm torn between thinking it's a waste of mental energy and feeling like I'm leaving money on the table if I don't optimize.

Surely this is a solved problem? But then I realized - none of the "smart" financial apps actually make decisions for me. They just show me information and expect me to optimize, but I want something to actually just DO IT and absolve me of that mental burden completely. It seems like we have all the necessary data, so why isn't this automated yet?

I'm curious:

1. Does anyone else find this constant decision-making exhausting? 2. Are there technical/legal reasons why our financial apps don't just make optimal choices automatically? 3. For those who do optimize heavily, what's your system? Is the effort worth the reward?

Maybe I'm alone in this, but I'm tired of seeing something so manual that, in my opinion, software is more than capable of solving.