Re: From 2 weeks to 5 days.
I would say first and foremost to pace yourself because you won't be able to do everything that you normally get to do on your regular Disney trip. Make a list of all your must-dos at every park so you can hit all of your favorite attractions at least once.
Also, it will help if you do a basic plan before you get there so you can get the most out of your days there, especially if you're staying on property so you can take advantage of Extra Magic Hours.
Re: From 2 weeks to 5 days.
I agree. Make a plan of "don't misses" - maybe one per land and then if you get to do anything else, it's great.
Re: From 2 weeks to 5 days.
I've actually never been longer than 5 days. All of my trips have been 3-5 days long. I do one day per park and one day for shopping at Downtown Disney and the Boardwalk, but another good idea would be to use the fifth day to do anything you missed during the previous 4.
Re: From 2 weeks to 5 days.
Though Id add, I am getting a 5 day park pass, however since I am comeing of a (non :() Disney Cruise I will have the rest of the day for shopping and resort touring, things like that. I also have another full day I am not getting a pass for, however I might be forced to go to Univerisal (I could debate about that).
Re: From 2 weeks to 5 days.
Most of my trips have been for around 5 days. I take some time before my trip to schedule out my days. I tend to stay away from the parks which are having extra magic hours, which cuts down on the crowds and waiting times. The only excpetion being if all other parks are closed at that time and the EMH park is the only one open, then I'll go (ex: if MK has evening EMH, I'll spend the day at Epcot and then go to MK after Epcot closes). I also try to combine my visits to AK and DHS for the same day, as there aren't as many attractions there that I want to see, so they can easily be combined in one day. I do all of my shopping after the parks close, at Downtown Disney. Also, consider having more quick service than table service meals.