One question.... How much cheaper is it to stay off site in comparison to the value resorts? And is it not more beneficial to stay on site for means of transportation and other "perks"?
It depends, of course, on where you stay, as there are hundreds of options, from cheap motels to quality hotels, to rental houses and condos.
We have baby #3 coming in another 6 weeks or sooner, and in order to save money and accomodate a family of 5, I reluctantly decided for off property on our next trip in May 2015. We are checking in Sunday May 24, staying for 10 nights. Official prices for 2015 are not yet out, but the estimate, based on this year's prices, for 10 nights at POR, is around $2100 or so. Take off the normal 25% discount that they usually offer for Disney Visa holders, or the General Public discount, and we're now around $1600. I found a condo for about $60 a night before fees. After fees, taxes, etc, my grand total for the 10 night stay is around $870, or about $87 a night. So saving around $800. Of course, we will have to pay for parking now, so of that $800 savings, I need to subtract out $17 a day for parking, probably having to park on 7 different days.
Regarding the transportation perk for staying onsite, yes, that is a perk, but on the other hand, it's questionable how much time it really saves you. While I enjoy the convenience of just walking out of my room and going to the bus stop and enjoying the ride (the whole bus experience is part of the "fun" for me), by the time we waste time waiting for the bus, I imagine we could probably drive in from offsite just as fast, if not faster.
Once in a while, we may come out to the bus stop and find our bus already there waiting for us to board. But more likely, we get to the bus stop and then wait a few minutes for a bus to our park, say, Magic Kingdom. After a few minutes go by, here comes a bus, but it is for Epcot. A minute or two later, here comes a DTD bus. Then a HollyWood Studios Bus. Finally, here comes a Magic Kingdom bus. We load up, but then have to stop at the remaining bus stops at our hotel and sometimes we even have to swing by another resort. If there is someone in an electric wheelchair, now we have to wait for them to open the other door and for the ramp to VERY SLOWLY descend down, for them to get the ECV onto the bus and then secure it in before the rest of us can finally get on. Long story short, even without an ECV, I have waited at a bus stop for 15-25 minutes on different occassions, and I'm sure that in that amount of time, we could probably just get in our van from our condo and drive on in and get there quicker.
Then, there is the issue of leaving the park, especially if it is around closing time and everyone else is leaving too. You get to your bus stop and there is a huge line for your resort. You wait and wait for a bus, and when it finally comes, you can't board because it fills up and you're still in line. Here comes the next bus, and it still fills up and you're still in line. So you wait until the 3rd bus, and finally you can board, and just hope there is no ECVs at your bus stop. In the amount of time you just wasted waiting on that bus, you could have been in your car and back at your offsite lodging already.