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.