I find it to actually be harder to keep Bebe out 24/7 in winter, summer is dead easy though.
I go to the yard twice a day every day regardless of the time of year and whether Bebe is stabled at night or out 24/7. In winter my morning checks usually involve changing her rug & picking out hooves at the minimum. I can do this in the field but have to bring her out if she has a morning feed. As we can't feed hay in the field she has to come onto the yard for a few hours to have hay so that means bringing her in or paying for the yard staff to do it in the afternoon. Evening check involves feeding, changing rug again if necessary, picking out hooves, etc.
Because hay isn't fed in our fields it actually costs me more to keep Bebe out 24/7 in winter as I end up paying for her to be brought in for a couple of hours each day to have access to hay. Because of this I decided to stable her overnight instead which she actually seems very happy with. It also saves me trekking up the 45 acre field in the mornings, through the mud, rain, wind, fog, etc to find her.
If we could feed hay in the fields she would live out. I have done this before and found it to be fairly easy. It's just the weather that gets depressing.
I do get up extra early to make sure I manage to muck out before leaving the yard for work. If I have to muck out in the evening I struggle to ride, so I prefer to do it first thing so I turn up at night and can bring Bebe in and ride as everything is set up ready for the night.