I'm a single mom, DS is all grown up now but we started going to WDW when he was 3. We stayed at the MK deluxes, only because at the time they were the only hotels that existed, GF hadn't been built yet. We stayed at what is now Shades of Green but back then was just a Disney hotel so we had to take the bus. I didn't take a stroller, little guy liked to walk most of the time but I'd rent one of the Disney strollers, and put him in it when he got too tired. He was one of those kids that feel asleep as soon as he got in a moving vehicle, worried me to death when he started driving. Soon as we got on the bus or monorail, he was in my lap and out like a light. Since I didn't have a stroller to deal with, I would either carry him or wake him up for him to walk. I didn't take a huge bag, just an over the shoulder tote type bag with a pack of wipes for dirty face and hands, ponchos and my wallet. No MBs back then, I don't even think you could charge back to the hotel. We really didn't need to lug around a bunch of stuff, no toys he was at WDW for goodness sake, he could run and climb and play there. We usually went back to the room for awhile for him to swim, and maybe rest but he wouldn't nap (Mommy may have). We didn't normally stay too late, he and I would be dog tired by around 8 and back to the room, since FP hadn't been invented you stood in line, sometimes for a hour, he was pretty good about it and would occupy himself talking to me, watching people, chatting with other people in the line or trying to pick up girls (he was a little romeo). It's not hard to do, just don't try to do too much, take your time and don't push. If he wants to ride the carosel 10 times ride it 10 times. If he wants to only eat french fries for lunch, go with it. If he's tired go back to the room and rest.