Originally Posted by Mike Jacoubowsky

Yes, he can probably get away with it, if he does it entirely without human intervention. If someone at United caught wind of the intent, it would not be reasonable to expect appropriate notation in his record and possible repercussions.

The procedure itself is relatively-simple; he checks in a T24 and immediately tries to get on a flight that day (a day ahead of his original flight). At the beginning of each new leg, he has the opportunity to attempt an SDC for up to 24 hours later than his current time. In theory, you could barnstorm the country with a series of overnights on a massively-multi-leg itin. Interesting scenario. To do this well would require a fair amount of planning (assuming multi-overnights; a single overnight at a hub would seem pretty easily accomplished).

Perhaps a record could be established for how many days someone could take, on a normal fare, for a transcon. Rules would require no MX or WX issues. I'd have to do some research on SDC rules; I think, but am not sure, you can sub a two-flight segment for one? In which case you could start with 4, and multiply them as you go.