Is the cheepest really the least expensive?

Usually not in my experience.

Example 1: I've been dealing with a carpenter at $20/hr for weeks now and he never seems to get much done unless you're looking over his shoulder. Now what good is that. If I'm paying him to do a job shouldn't I also have to factor pay for myself to supervise him if he needs it. Humm seems like I could have gotten a better qualified contractor to do the job for what I've paid in our combined time and hours.