Done Disney basically every way possible. From All Starts, to Concierge at the Poly. From a variety of Hilton Brand Hotels, and even rented a house once (before AirBNB). When we were younger, we stayed with a friend’s mom up by the villages.
It is all about what you want.
We own at BLT, so, yeah, we do like staying on property, with the ability to walk to the MK. And with DVC and AP, we do not pay for parking. We drive to the world, so, we do have a vehicle with us.
As someone else stated, yes, if your party is going to split up, staying on property is much easier. And while ME may be gone, you can always uber to and from the airport. Trust me, it is quicker. However, if you are all together, staying off-site can be much cheaper.
Since we have our car, and parking is included, yeah it is easy and cheaper to stay off-site. We tend to do our annual week-long trip staying on property. We tend to take 4-6 long weekend trips and stay off-site.
With the ability to work from home all the time now, the one thing we have not yet done is rent a house for a month. Thinking that may be pretty kool to try. Let friends/family visit as they want. Do Disney like a local. Head to Paris for Dinner, or quite frankly, up to space...