I went to Disney World (Orlando) 2-3 years ago. I was at Disney Land (Cali) 2 weeks back. For both of these visits, it was my first time. My suggestion to you is as follows. Stay on property, and get the dining plan.
We stayed on a moderate hotel when I did DW. However, when we go back (GF goes like every 12-18 months with family) I will be staying in one of them on the Monorail system, like the Contemporary. I would prefer the convenience, especially staying for a week.
