If you've got grade school or younger kids or senior citizens in your travel group, taking a midday break is SO worth it. As mentioned, it's easier from the 3 parks besides MK and/or when you plan to park hop later anyway, and also easier when park hours are pretty long. The parks are not only physically tiring with a ton of walking, but the amount of stimulation in the parks can be fatiguing. A quiet resort break for a nap or time to unwind and play/swim freely can do wonders for everyone's attitudes and enjoyment of a parks-centered vacation.
If you want to enjoy the lower crowds at RD as well as the nighttime fireworks and light shows, then a midday break is almost a necessity, IMO. The choice is then between "Lose a few hours of valuable park time midday?" vs. "Wear out family members and have possible meltdowns in the evening?" Realistically, we've sometimes taken 3-4 hours out of longer days to allow for transportation and really recharge. Mid-afternoon lines are long anyway. We've found it takes us about the same amount of time whether we've stayed onsite and waited for transportation or walked to our car and driven directly to our onsite or offsite resort and walked to our room. At Windsor Hills, you'll be parked right outside the unit so you won't need to make a long trek back to your room from the car or rideshare. Yes, totally worth it.