Buying the cheapest does not work for me. I have tried, so many times, to get the least expensive version of something, but I end up disappointed. I end up spending more time trying to fix or exchange the item than actually using it. Here are my personal examples:

• My first computer, a Cyrix (remember them?) based computer. A 200Mhz Pentium clone. It was slow, and if you ever tried to do anything with the onboard, software based modem, it lagged and dogged like no one’s business. Why did I buy it? It was the cheapest Microcenter had at the time. I learned my lesson, build your own, or buy a nice, mid level computer instead. Since then, I have always built my own, since then I know what parts are inside, or, purchased a mid tier laptop.
• Shoes. I don’t know how many pairs of shoes I have gone through. Every time I think I am getting a deal, I get a shoe that lasts a year and hurts my feet at the same time. Some people can get away with inexpensive shoes, I can’t. I won’t even mention how much I paid for my last pair of shoes, but it was worth it. Almost no foot pain and a pair of shoes that should last 10 years, easily, and I can get it resoled from the manufacturer for $65.
• Watches. I have gone through my fair share of Timex, store brands, etc. Most only last a few years, and when you change the battery, it costs a good percentage of the watch price. Give me a good watch any day from Seiko or Orient. They will last decades and are worth the little extra money.
• Furniture. How many of us have owned a futon? How many are still in working order? My guess is not many. I have tried to go cheap, but the stuff just does not last as well. Get a good Flexsteel or name brand, made in USA couch and it will look out of style before it wears out. Same thing goes for mattresses. Coffee tables and book cases you can go cheap, but nothing you can sit or sleep on.
• Electronics of many sorts. DVD players, wireless routers, USB card readers, etc. I have bought the cheapest of all of them and had to return or replace just about all of them. I should of just bought the better model to begin with.
• Cookware. A cheap pan works like a cheap pan. A cheap knife cuts like a cheap knife.  Cheap spoons bend in ice cream that is not soft serve and I really don’t want a piece of mystery metal in my mouth when using a fork or spoon otherwise.

So much time and money wasted, when I could of just bought the better version of something. That is not to say sometimes the cheapest version will not work just fine. If it does for you, more power to you. Some things don’t really seem to be much different quality, no matter the price, like blank DVD’s, most clothes and toiletries. It all depends how you use an item, I guess. I try not abuse anything that I own, but I expect it to at least meet some minimum standards. However, I am opposed to ‘buying the best’ since ‘the best’ is usually 10 times more expensive and works 5% better than the mid tier version of something. A little more money spent up front more than makes up for the lack of heartache later.