Really? I am sure Dustin can speak for himself but I would have thought it obvious that is impossible to objectively assert that something is the best and that when you say that something is "the best", you are implicitly solving a matching problem given your constraints.
In general, I am not convinced by your case as to why getting something that you personally think is the best is so bad. Sure, there might be some people who would worry about the best getting damaged or whatever. Then again, I would argue that your matching algorithm should choose something that doesn't get damaged so easily. E.g. One of the best investments I made was in getting a pair of Shure in-ear headphones. They weren't the most expensive I could have got but they were five times as expensive as the skull candy crap that I get. Guess what though? They have lasted me 5 times as long. Sure, there has been some change in the way I handle earphones but still there are many days where I close my laptop and remove my earphones and leave the entire setup on my bed and go to sleep.
Having said this, I get the idea that the cognitive load created by having to make decisions about what to buy can be annoying at times. I have been putting off the decision of buying a bike because there is so much research to do.