If I were in your shoes...I'd take a moment to price out the comparable value of each option for the dates you want.
Also important to note if you are considering a 3/2 split is that the hotel rates are usually higher on the weekends, and the price differences tend to be greater at the deluxes. so you might want to make sure your free deluxe nights are weekend nights, even if that means deluxe then moderate.
Last summer we really liked the Coronado Tower, but we stayed club level, and had a car. The one time i tried to get food in the main food court it was terrible. the smaller grab and go quick serves were a little better, but limited. the main food court used to be great years ago. The food court at Art of Animation is pretty good, or was when we visited (we actually drove their to eat one night).
The downside of the big WDW moderates - CSR, CBR, and POR is if you don't have a car, you lose a lot of time waiting on transportation, and taking transportation. AKL and WL are in between (love them, wouldn't choose them in this case). We love BC/YC and CR. While CR doesn't have the theming, it is convenient for getting to MK. A second plus of the contemporary is that you can easily access all eateries on the monorail hotel line.
The upside, IMO, of the mods is that the theming is nice. I haven't stayed at CBR in many years, Other than the food court being meh, CBR is very pretty. (and I'm pretty sure Club Level is still closed.) BC/YC has a super pool.
So...most likely , if I was in your place, I'd pick BC, YC, GF or CR, and probably paired with AoA. Or right now maybe one room is best. Maybe 4 days instead of 5 as a potential option?
We've done lots of split stays. they are easy if you pack right and don't unpack a ton at each stop. Mostly we just unpack toiletries at each stop- daily essentials. Things we only might use (over the counter meds, moleskin) stay in a giant ziplock bag until we need them. We otherwise live out of the suitcases. As much as possible, we just open the suitcases and put them on a luggage rack, or on a countertop/desk. Dirty laundry goes in a bag that doesn't get unpacked at the second hotel. WDW hotel will let you drop off bags at any hour, or we leave luggage in the trunk. The only hard part is moving something perishables and chocolate. for some reason WDW = chocolate. I sometimes bring a softsided cooler that keeps stuff cold. Soda cans actually make a decent kinda cold pack. not as good as ice packs, but refrigerated soda cans stay relatively cool for quite some time. not cold enough for milk, just semi cool, and not as well in FL summer.
One plus of splits is you an hit parks based on where you are staying. Take advantage of being close. If GF- go ot MK and GF eateries thsoe days, for example.
