Nice, the $1000 travel savings is quite smart. Nobody i knew did that.
Now, I am just quoting someone with no verification, but apparently, at some point in time (maybe still?) Southwest sold system-wide, anywhere, anytime walk up passes. They were not cheap, but well bellow what someone would pay for a full Y walk up fare on a real airline, and didnt really expire. This was years ago.
His parents used this as a get out of jail free card when non-reving on NWA.
The flights are getting fuller, capacity is getting cut, and america is getting fatter (believe it or not, some flights actually go out a seat or two short of a full load due to the newer FAA passenger weight rules!!), but as long as you are willing to go where nobody else wants to at a time nobody else wants to, you are probably fine.