I find it's well worth spending money on reliability and low maintenance for things you use regularly. I cycle as my main form of transport, and I spent extra money on a good set of internal hub gears. The only maintenance required is a yearly oil change. The time needed to clean and adjust derailuer gears probably isn't much, but the subjective feeling of reliability is valuable for me. Likewise, I use tires with strong puncture protection. I'm confident that I can set out to cycle at short notice and arrive at my destination at a predictable time.
The same principle applies to computers, eg. reducing the number of moving parts, having good filters at air intakes, buying reputable brands for parts even with no direct performance benefit (eg. power supplies). I have less computer problems than people I know who buy purely on cost:performance ratio.
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.