The thing is, a lot of the advantages you get from money can be had on the cheap if you are reasonably resourceful. For example, it may be awesome to go out with your family to a fancy restaurant for dinner. But it's almost as awesome (and in some ways more awesome) to plan and cook your own nice meal for your family. At far less expense.
(Note I am referring to your typical middle class American here.)
I do agree that saving on commuting time and inconvenience is worthwhile if you can afford it.
Depends if you like cooking, and if you have the time to do it properly. There's a reason you pretty much only see childless folks Instagramming dinner.
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.