Imagine nothing but toll roads.

I subscribe to The Simple Dollar (because it's a neat blog with pretty good advice) and in the author's most recent roundup post was a link to another post, at another blog, with the subject line "The Hypocrite Test: Should Rich People Pay More?" I cleverly deduced had a feeling that this post was about taxes somehow, so I clicked on it.

I was correct. The author of this post begins with the following scenario, in which the reader is supposed to imagine that they've been working hard for twenty years, and have gone from having nothing to having a very nice house in a very nice part of town (where they now live with their family and their possessions, some of which are also nice.) This nice new house needs a nice new boiler, because apparently the one it came with was not so nice. So they call a contractor, who:

...pokes around a bit, then hands over a proposal. $15,000. Youch!

Sounds out of line, so you thank him and send him on his way.

Later that day, you run into an old friend who lives “down the hill.” You mention your need for a new boiler and are surprised to discover he’s in the market for the exact same boiler. And, the one he’s replacing is the very same one you have. AND, he also just got an estimate from the same contractor…for the exact same amount of time, same equipment, same job.

But, your friend’s estimate was $7,500. Half of yours.

The author asks if this scenario is fair or not, and specifically tells the reader to think about why it is or isn't fair and keep that line of reasoning in mind. The author then goes into the next scenario. Guess what it is.

This time, you’re the guy living down the hill, earning a modest living. The contractor is now the government, the estimate you and your wealthy acquaintance received is your tax burden and the benefits are the services provided to both of you by the government.

The instinctive conclusion that many readers will come to is that neither situation is fair. This makes sense if you assume, as the author does, that these to situations are "the same issue, just set in a different context" - a transaction is fair if you get what you pay for, and since taxes don't work this way then they must not be fair. I was tempted to make this assumption as well, but when I took the time to consider the analogy, I realized that it was flawed.