The major benefit to me is familiarity. And probably transportation.
During the 70s we stayed with family and did day trips to MK. During some of the 80s we stayed at off site motels ‘right outside the gate’ and did day trips mostly to Epcot. I don’t think we ever stayed at the same place twice.
In 1988 we tried on site, parked the car in the lot and never looked at it in 3 days. Had a blast. Since then we’ve stayed another dozen times on property usually different resorts, mostly deluxe and villas. Stayed off property a few times - vrbo 5br house, DoubleTree DS one bedroom suite, Cypress Pointe - three 3-br villas.
We’re used to what Disney provides in lodging. The off site properties have mostly been a disappointment. They’re just not right somehow.
Too soft, or too small. Cypress Pointe was the exception, except no Disney transport.
One memorable trip - first week in June. Already way too steamy at 7 am for my sister. It’s no coincidence she owns a Grumpy t-shirt. I’m thinking, it’s going to be a long day. We get on Disney transport and what’s playing? I Just Can’t Wait to Be King. Within about a second and a half she and her adult DD are having the best. day. ever. Problem solved.
You’ve got your own vehicle with your own tunes? And you probably have a nav system. As do we. However we’re challenged in some regard we’ve not been able to figure out.
We get lost. Always. We’re going to Epcot - how come we’re driving into Art of Animation!?! Another trip, trying for Beach Club, here’s Epcot AGAIN. We did that trick 3 times.
We NEED Disney transport. We like Disney lodging. I’m quite happy for folks to save money and time off property. Really. 