I used to work with a guy who was in industrial sales and had customers all over the US. He lived in Connecticut and would schedule the first flight Monday out and last flight Friday back out of a York Airport every week just to get on the fullest flights and have the greatest opportunity to take a bump. He was very successful at this and always had tons of credit that could be used for leisure travel.
The difference to what the OP has suggested is this person actually had business and intended to fly. He just did not have to be at his destination or back home exactly on time. Second, he usually took his scheduled flight even in a highly likely to overbook situation. The OP plan may work occasionally, but overbooks are more rare than one might think and most times are cleared with people taking low offers.