What are the real benefits these days to staying on property?

Our issue with staying off-site is when there is travel during the day back and forth to the hotel. If you can get out in the early AM and stay out until you are ready for bed, then staying adjacent to WDW would be fine.
 
We go for a week every few years. 60+10 ADRs, convenient park aces, and Deluxe Extra Hours are things we takes advantage of. And Early Morning Magic does get you ~2 extra rides in before the lines get real crowded.

But, in the context of a "quick weekend trip", I wouldn't hesitate to stay off-property with the intention of spending full days in the parks and eating QS. That's when you just go into park commando mode and press through until it's time to go back to the hotel and crash.
 
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We go for a week every few years. 60+10 ADRs, convenient park aces, and Deluxe Extra Hours are things we takes advantage of. And Early Morning Magic does get you ~2 extra rides in before the lines get real crowded.

But, in the context of a "quick weekend trip", I wouldn't hesitate to stay off-property with the intention of spending full days in the parks and eating QS. That's when you just go into park commando mode and press through until it's time to go back to the hotel and crash.
Hi there, I have 4 kids, now 25,23,20 and 18. I also have a handicapped sister and a niece, now 26. For years when they were little, we would take advantage of free Disney dining or discounted onsite rooms and go for a week every year. The last time we did an onsite trip was in 2018. We have stayed at all the resorts from the All-Star Music to the Poly. In 2021, we stayed at a house near Disney. We had such a good time. Yes, we did get caught in traffic and yes, we missed staying at the Poly, but we had 4 bedrooms, 3 baths, a swimming pool and a game room. We were able to do laundry and we could make our own meals. For us it still was worth it to come home at 12:30 and then go back at 4 except for the Animal kingdom; that was an all-day park due to the hours. We scheduled dinner at the Poly and every year we go now, we have dinner at a new resort. We have also included boyfriends and friends so our group can get big and when I bring up us staying on site, everyone screams "no". Some of the offsite homes are decorated so nicely. For us it just works better. You have a smaller group, so you probably still benefit from staying on site. But someday, when there are spouses or friends coming, try offsite. Enjoy your stay because no matter where you stay, Disney is the best!
 

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