I have done both we stayed on property about 12 years ago for our honeymoon and it was great. But since the kids have come along we stay off property. For a couple of years we stayed in the normal hotels which were great at the time. But then we started staying in the condos much better. Vistana resorts was great we also have rented other condos you can find great prices especially if you need 2 rooms. Plenty of space etc. This year however we are going back on property to the WL for Christmas should be great. We are giving ourselves a treat this year. I truelly believe it all depends on a families budget. If you are limited like we are most of the time off property is the choice because you can save money on the hotel and put that towards your tickets etc. Because we all know once you get to a park you just don't want to ever leave. We have gone to WDW for as low as $800 for 5 day park Hopper 6 day hotel plus food for 3 people. It can be done you just have to plan. Just to say we did everything that we wanted in that trip and had a great time. But we also had the use of buying our tickets from the military which saved us about $150. But everything else anyone could find. My advise is to think about what you want to do and plan accordingly.