We almost always stick to carry-on unless it is a long trip. Then we maybe check a shared carry-on bag.
We always bring 2 pairs of shoes per person, where at least 1 is water tolerant. (Usually quality walking/water tolerant sandals and sneakers.)
On a recent trip, we got stuck doing laundry twice, which was unusual. We normally avoid it.
It was VERY easy to do laundry at Stella Nova! We started a load just after 8pm. Laundry room was a few doors down, very clean. It was $4 for washer, $1 for detergent, and $4 for the dryer. Room key required to enter.
Doing laundry at WDW hotel was harder: much longer walk out in the cold, later at night, laundry room less clean, and even at 11:30pm, most machines were still in USE! Upside was someone offered us free detergent.
I recently completed 17 nights that were supposed to be 16... thanks, winter storm and AA. I ended up not wearing a lot of what I packed. I never learn my lesson, haha! I did laundry once at Boardwalk, once at Riviera, and once on my planned final night at OKW, only for the novelty of having a 1-bedroom with in-room laundry. I hang dry my jeans and shirts, so I had to plan in conjunction with my split stays. I won't be doing that again either.
Due to the variance from super cold and windy days to 87 degree weather, I just packed too much. I ended up using some of the vacuum-sealed space-saving bags, and overall, they were great, but they have their drawbacks. For one, when compressed, they become rock hard. This meant I had to be strategic so I could close my suitcases (plastic shells) without them bulging too much and putting stress that could cause cracks in transit. Also, since I stayed in so many different rooms, it meant only unpacking for the 6 and 7-night stays. The single nights I left them mostly packed, but it made accessing clothes for the day a pain.
My goal next time, if I can afford to go back, is to pack around 40%-50% less. I had 3 different jackets of various styles and warmth because you just never know. I don't want to be too warm and carrying around a jacket all day, or be too cold in the evening and underprepared. Then there were the few times it rained and I needed my third jacket that was more heavy duty and waterproof with a hood. For reference I always go in mid January because the FL humidity and heat is so unpleasant for me that it is a deterrent.
I ended up packing a small duffel bag in my suitcase so I could use it to take clothes to and from the laundry rooms, as well as put my
Walmart haul in it to go from hotel to hotel. This was very helpful but also took up valuable suitcase space. A week prior to my trip I caught a mild cold which I fought and beat, but paranoid me packed all kinds of cold meds and saline nasal spray among other supplies for theme park injury and illness prevention. Definitely overkill but the sundries offered at Disney hotels are so limited. They didn't sell lotion that I saw and for whatever reason Gran Destino Tower didn't have any in the room. Things like that I either brought or acquired on my Walmart run. The former boy scout in me abides by their motto: be prepared!