Oh heck yeah!! We never stay on property, we always stay off. I'm not going to slam anyone who does. If my wife and I were going by ourselves for just a quick weekend trip, and we had money to burn, we'd consider staying on property, but even then probably wouldn't. We went alone for our 10th anniversary and stayed at a Sheraton (not the Vistana).
First and foremost, it's cheaper. Way cheaper. We rent nice places for between $650-$800/week. By nice, I mean 3 or 4 bedroom, 2 to 3 baths, full kitchen, full amenities we'd have at home. Don't think you'll find anything even remotely close to that kind of value on property.
We're a family of 5. I love my kids to death, but the 5 of us in one hotel room for a week would not go well.
Wife and I are big time fitness, bodybuilding nuts. Our nutrition is very specific. On vacation, I'll relax it a little, but still could never eat out every meal. Just wouldn't work for me, and my wife would flat refuse. Having a kitchen is fantastic!! No, we don't spend hours cooking and cleaning. We may spend 10-15 minutes in the morning packing lunch and on one of the nights we're home chilling, we throw some chicken breasts in the oven. So "cooking" isn't work, just takes a few minutes. That also adds to making staying off property so much cheaper than staying on. Since we pack 95% of our food, we're just paying grocery store prices, like we do at home. Saves a fortune over eating out, even with the
Disney dining plan.
We can have fresh clean clothes at our convenience. Again, it's not hours of doing laundry. It takes a couple of minutes to throw stuff in the wash/dryer.
Multiple bathrooms is incredible to have when you've got a family of 5. Makes getting ready and getting cleaned up so much easier.
We have room to spread out. We spend a ton of time in the parks, but do take some time to chill out at home. We'll use the pool at the community we stay in, which is typically a very nice place and nowhere near as crowded as a hotel pool. Plus, the condo or townhouse has so much room for us to spread out and relax. My boys can go into one room to watch their TV, my daughter her own and my wife and I get peace and quiet. That's absolutely invaluable, and something we could never get in a hotel room. Or you can spend great family time together. Perfect example is last Thanksgiving. We were in MK in the morning/early afternoon, then went "home" to our condo. We had the local Publix make us a full Thanksgiving dinner with all the trimmings. Cost far, far less than any restaurant would charge. We didn't have to cook. We sat down at our own dining room table and had a wonderful family meal together. Then we sat in the family room and watched football. Best Thanksgiving ever.
We always have a car with us. I'd never want to rely on Disney transportation. We can come and go as we please and go anywhere. Only time it really "adds" to our time is at MK and it's really not a big deal. But we can go to a store if we need supplies, or very often we go to Dunkin Donuts or Menchies for dessert. We also frequent the gift shops on Rt. 192.
At least for us, it doesn't diminish the experience in any way whatsoever. In fact, it adds to it by giving us so much freedom and flexibility. I just couldn't see how we'd ever make it work to stay on property, nor would we want to.
As for where we stay, we've tried tons of places. We stayed at Sheraton Vistana, many years ago. It was really nice. Our favorite place is Villas at Seven Dwarfs Lane. It's only a few miles from Vistana. If you leave Vistana, go past Disney entrance (Rt 536) and keep going. You'll come to the intersection of Rt. 535 and Rt. 192 about 1.5 miles up. Turn left at the T intersection and Seven Dwarfs is the second traffic light. Takes less than 7 minutes to get to Disney entrance. We use VRBO to find our place. There are SO many nice places along Rt. 192 to choose from.