Years ago, we would drive into Orlando in the early evening and stay off-site that first night. We then would get up very early the next morning and make our way to our WDW resort to check-in and get our length of stay passes.
Now, we won't even consider staying off-site. This is for a variety of reasons. Primarily, we like waking-up at our resort and heading off to the parks with no delay. Also, staying off-site is no longer as cheap as it once was. (We used to stay at a Fairfield Inn for really, really cheap. It is now over a $100/night.) I know there are bound to be some inexpensive motels close to WDW, but I am no longer willing to take my chances and end-up staying at some ratty hole-in-the-wall. Since we are AP holders now, the discounts on rooms generally make it far more affordable to stay on-site. For our Christmas week trip, we were able to book a value room for our first night for only $59.