What a shame that no one has replied to your post yet. I have stayed off-property for the past 5 times I've been to WDW and there are some definitely pros to this arrangement. Yes, driving out of WDW at the end of the day might detract a little from the overall experience, but the vacation homes are so incredible that it definitely makes up for it. We have been traveling with babies for the past 6-8 years, and it's SO nice for the baby to have her own room with a standard size crib (we have rented). It is great that everyone can spread out into their own bedrooms, and a full-size kitchen is amazing and economical. And having a private pool makes the trip completely magical for all the kids.
We have stayed in Windsor Hills every time we have rented a vacation home, and we have always done the research ourselves and rented through VRBO is Vacation Rentals By Owner. Windsor Hills is amazingly close to the WDW gates, and the community's amenities are incredible. They have a gorgeous pool, a game room, security gates that are manned 24/7, even a tiny movie theater!
I can't say enough about how much we have loved our rental homes. They have been decorated Disney through and through. They are clean, HUGE, and have tons of things for kids like DVD's, game rooms, toys, video games, even dress up clothes!
I could go on and on.
Obvious cons, you are aren't on Disney property. Rental car is a must, which means paying for parking. You can't take advantage of Extra Magic Hours. And there is a little removal of the whole experience at the end of the day. We are staying on property this year for the first time since 2003, and I am very excited to have that Disney Magic experience.
Buy for me, the pros vastly outweigh the cons, especially the price and the amenities if you are traveling with a large group.
Please feel free to send me a PM with any questions. I'm - obviously - always happy to talk Disney!