As I've gotten older I've realized that mostly you get what you pay for; buying cheap stuff, generally speaking, is a short-term win with long-term consequences. For example a cheap appliance will tend to die faster, so you need to repair or replace it and probably will wind up paying more over time than you would have if you'd have spent upfront. (Of course some would argue that keeping the capital on hand would net you potentially better wins - but most people aren't investing every spare dollar, let alone in a smart way.)
There are other benefits to spending up, like more functionality. I've been thinking about this every time it's snowed this year. When I bought my house a few years back, it was the first time in my life that I had to get a snowblower -- I grew up and lived in condos and apartments and so never had any driveway to clear. So when it came time to buy, I got one of the cheapest ones available. It wasn't that I couldn't afford to spend more, but I figured why would I spend money on that? Now I regret that decision immensely, and every time I visit Home Depot I stare longingly at the high-end Ariens models and wish I'd dropped three times as much.
So I'm curious to hear from others and perhaps avoid future errors. What are things you wish you'd spent more on, and why?