For me, it almost entirely depends on the amount of use something will get. I, for one, rarely wear dress shoes so I have a few cheap pairs to go with the few dresses I own, and which will work for any occasion which would require dress shoes. But my everyday shoes are, for me, rather pricey. But I've had one pair for over 6 years now and they're still going strong, even though I spend a lot of time walking. They're still comfortable and still supportive, so the price was worth it.
We will almost certainly be moving out of our state sometime in the next two years, also, so that factors into decisions. The less stuff we have to transport, the less expensive and generally easier it will be. My husband and I have talked it over and decided that there are two pieces of furniture we'll take with us when we go, everything else we'll either sell, give away, or take to the transfer station. It sucks having crappy furniture for now, but the long-term goal is far more important to us. Once we're definitely settled in a place, then we'll invest in comfortable furniture which won't fall apart within a couple of years, doesn't require zip ties to stay together, etc. :) I'll be far more upset to part with my plants than I will be to get rid of our furniture.
