Still, you cannot just learn at will to find arbitrary things fun.
Actually, I can if I put effort into it. Especially if the activity has a purpose for myself.
But even if you can't, you won't know how an activity will feel after a year by taking a lesson in it. My first month of dancing Salsa was horrible. In the Salsa community the first months for males get called "beginner's hell". If you only engage in hobbies that are fun the first time in which you engage them I don't think you optimize happiness and more importantly you probably won't engage in activities that challenge your weak area's in a way that makes you improve on a more general level.
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.