I HATE lugging a bunch of luggage through airports and trying to find overhead space, so I check bags whenever I can for free. I even pay the $25 on occasion when I could probably manage with just a carry-on, just to avoid the hassle.
So if I were you (which I fully recognize I'm not LOL), I would take full advantage of the two checked bags. I have a large rolling duffle bag that I use for both DD15 and myself on trips. I can usually fit all the stuff we need for a week or more into it, and hit just under the 50lb limit. I don't use packing cubes or anything else - DD15 and I don't exactly like the same styles, so it's easy to tell our clothes apart. I am also a fan of rolling our clothes, and packing cubes just end up wasting space in that case.
Carry-ons I keep to just what we need for the day. I have a long history of lost luggage, and even so don't bother with a change of clothes in our carry-ons or anything like that. I've had my bag gone through at the security check point to check out items they can't see clearly on Xray before, and the thought of them pulling out my unmentionables in full view of everyone there just makes me cringe

(Hey, I didn't say my fears were rational! And yes, I know that can happen with checked baggage too, but at least I am not there to see it!!) I figure I have a credit card - if no luggage appears, then I'll hit a Target or
Walmart and buy what we need. The one thing I do make sure to have in my carry-on is any meds we need, and any electronics and jewelry that someone might be tempted to steal from our luggage. Unfortunately, that has actually happened to me in the past.
One other thing - you might want to consider bringing only enough clothes for half your trip, and just doing some laundry while you are there. I find it a nice "timeout" from all the Disney go-go-go. We just hang at the pool, hit the gift shop, etc. while our laundry is going. DD and I also have a tradition of splitting a handmade ice cream cookie sandwich at some point during our trip, and this is a good time for it. With multiple machines, it goes faster than you would think.