anything that goes across the web...can be intercepted by someone with the right software

True.  But in the examples you cited, the person intercepting the information has to engage in some sort of active pursuit (assuming you don't have very poor security practices).  Using an anonymous proxy is just willfully handing over the information.

Kind of like handing your wallet to the pickpocket before they try to touch you.

Being fast and saving money are important, but always secondary to the primary objective.