Hi! I've posted the detailed pros/cons of land/sea in a few locations on this board, but will give you the quick points here:
TICKETS - About the only way it financially makes sense to do land/sea is for the tickets. You can add the no expiration option for about $95. We did this in Jan. 2006. We used only 2 days and came home with 5 remaining on our cards. This way our tickets for the next trip are already paid.
DINING - The dining package is currently not available with land/sea.
ROOM/STATEROOM - land/sea requires a link between your resort room level and stateroom category. For example, to get a Cat 3 stateroom, you must stay at a delux resort. Not everyone likes this mandate.
LUGGAGE - Land/sea is priceless for this. Check you bags in at your home airport and don't touch them again until they arrive in your resort room. The day you leave for the cruise, have them picked up around 8-9am and not see them again until they arrive in your stateroom. If you have transfers back to the airport, you can check them in for the airline at the port terminal and they magically arrive at your home airport.
GETTING TO PORT - With land/sea you take bus transfers from the resort, which is problem-free. You don't get to the ship until 1-2pm. Some like getting there earlier. FOr this you need a rental or towncar.
We did 3 night land/ 4 night sea as a Ph.D. grad gift to my friend and wanted no hassles. The problem was we ran ourselves ragged at the park and were a bit too tired during the cruise. It was my 17th WDW trip and I fell IN LOVE with the cruise. 4 nights was definitely NOT enough; I'm not sure why anyone does 3 night. I can easily say we have no WDW trips planned for the next couple of years; it's crusing all the way for us!
Happy to answer any other questions!
Gayle