The DL website will only book up to three legs each way.
Remember when building connections that anything over four hours is considered a stopover and not a connection so the fare will be broken at that point and priced as a circle trip, etc. The only situation that does not fit this is when you arrive into a city on the last flight from your origin and take the first available flight out.
Lets say you arrive in ATL at 8:00PM and the first flight out is 8:00AM. You may book this and it is not a stopover.
The only problem with this is that NO CRS system will do this manually. The res agent must force the connection. Most T/A's are not even aware of this rule either. Its a good way for an overnight visit with friends/relatives.
Im still hunting for a booking site that will allow a request for a fare quote on all airlines that will bring up the airlines fare basis codes. Looking at this one could see all the valid connecting cities on say an KE14SPNR $298.00 R/T fare. Let's say this fare was from Florida to NYCa on USAirways. This fare may allow connections in Richmond You could fly FLL-CLT-RIC arrive evening. Depart next AM RIC-BWI-NYC. This is a legal connection if RIC is on the routing. I have yet to find a Web site that will price it though.
Sorry for rambling
TW