Optimize vs YOLO

At what level of wealth do you have to be such that a decision that affects 5-10% of your net worth can be viewed through the lens of intangible values vs primarily a capital allocation decision? For context: my wife and I are considering a meaningful purchase. It’s a been a long struggle and has caused a ton of stress. We are down to two paths. Option A: is subjectively not our favorite but it is a great buy at a good price. Option B: something we really like it but it’s objectively much more expensive AND overpriced. The value destruction of option B is definitely in the 5-10% of our net worth. Think mid-high 6 figures. I’m trying to leave out specific details so as to not bias the feedback, but I’ll use a pretty representative analogy: a brand new AMG Mercedes SLS that which is sure to depreciate like a rock vs. a 20 year old Porsche 911 with a manual transmission that costs ~20% less which will not only hold value but may go up a bit. We are in our mid 40s and are on a high probability trajectory to $10M liquors NW (excluding our primary) in the next 2-3 years.