Depends if you like cooking, and if you have the time to do it properly.
That's two separate but related issues. I definitely disagree as to the second issue, as I doubt there's much more time involved in preparing a nice meal than in dining out at a fancy restaurant. Besides, it's not too hard for your typical middle class American to find a couple hours on a Saturday or Sunday afternoon to cook.
As to the first issue, I agree that there are probably people out there who hate to cook, even if it's an occasional special project. Still, those people have other options. For example, I have a family member who doesn't cook; is cheap; and enjoys fine dining. So he finds special deals like restaurant week in New York and enjoys fancy meals for a fraction of the normal price.
To be sure, one could come up with a scenario where there are no special deals available; one hates to cook; and all other options are cut off in some way. And while I agree that may happen from time to time, it does not seem to be the general rule. In my experience, there are usually work-arounds available.
There's a reason you pretty much only see childless folks Instagramming dinner.
What exactly is that reason, in your view? I can think of a lot of possible reasons which do not contradict my claim. I cook perhaps 30 or 40 meals a year with one of my children and it's never occurred to me to Instagram them.
You can generally keep the kids in line better at an Applebee's than when you actually have to watch the food. (Yes, I know Applebee's isn't a real fancy restaurant, but it's the sort of place most people think of when they think of dining out somewhere nice). And the real competitor to cooking is often pizza delivery or a drive-thru, not dine-in.
IMO, the reason for that is that the meals you want to show off are usually the fancy foodie sort. To pick my most food-photo-friendly friend as an example, she posts things like "My take on wing night: gril...
On ChrisHallquist's post extolling the virtues of money, the top comment is Eliezer pointing out the lack of concrete examples. Can anyone think of any? This is not just hypothetical: if I think your suggestion is good, I will try it (and report back on how it went)
I care about health, improving personal skills (particularly: programming, writing, people skills), gaining respect (particularly at work), and entertainment (these days: primarily books and computer games). If you think I should care about something else, feel free to suggest it.
I am early-twenties programmer living in San Francisco. In the interest of getting advice useful to more than one person, I'll omit further personal details.
Budget: $50/day
If your idea requires significant ongoing time commitment, that is a major negative.