If we go back in the afternoon, our day would be over in the parks. Anyone else RD and push through to an early dinner and call it a day? With a little, we can't really make nighttime happen.
I never take planned breaks; I'm RD to closing every day. But I have no kids, and I only go in the cooler months...
That's exactly what we do. We get there at rope drop and head back to the hotel after dinner. We always have a stroller for a quick little nap for our daughter if needed. It's worked for us for 3 trips in a row (ages almost 3, 4, and almost 5).
Depends on the time of year. In winter the parks close pretty early anyway so breaks are not really necessary unless you have very little kids.
In the heat/humidity, a break is almost required (for thick blooded northerners!). And the parks are open later so going back is usually fine.
We do this every August but we know we can't do consecutive park days. Need the rest/pool days in between.
Before DS came along, DH and I usually went RD-close. We've taken DS at 15mo & 2. We try to stick to his schedule, which allows for RD. He naps pretty well in the stroller, and then sleeping by 9. We were usually back to the resort between 7-8. The mid-day break wouldn't work for us. We have taken more leisurely mornings, though. DS is always up between 5:30-7, but we don't rush off to a park. We lounge around the room, go swimming, enjoy the resort, etc.
That will really depend on your little one... if they are the type who will sleep in the stroller while you have a meal or watch a show then I can see it working. If not then it may be more of an issue. It may also be a question of the adults and/or older kids' stamina... keep in mind that RD day is also a pretty early day, given that you'll likely be leaving the hotel room by 7:15am at the very latest (and that's if you're staying onsite) so even just pushing through to a 5:00pm dinner is going to be a 10 hour day, and while most people can do one or two days of that and some can do that every day, lots will start to poop out after a couple of long days and crabbiness/burnout can be a major thing. Physical exhaustion can be an issue, as well... in addition to the energy-sapping heat (which isn't such an issue for some people, but for others it's really a problem) there's just the sheer size of the place. In a typical WDW park day, even with a 3-hour midday break and 2 table service meals I still usually will take 20,000+ steps.
In the end you just have to gauge your family's temperaments and habits, and maybe plan to be flexible in case your estimation turns out to be a little off.