My number one rule? NOTHING medicationwise gets checked. Not only because of risk of delay, but theft (medication is target item) and not in the least; baggage compartments are NOT temperature controled. Or in simple words; they will be exposed to temperatures outside, including the freezing temperatures on tenthousands feet altitude. I am not gambling, hoping it will be no problem because my meds can take it or my baggage is not the one on the outside and most exposed.
So carry on is the only way. For my last trip that came down to 1.5 carry ons for medication. I'm also on tube feeding and temperature controled compartment is not even available on any possible itinerary on all legs. The quality can no longer be gauranteed in freezing temperatures, spilled feedings have been found before. So -> carry on. Yep...... read; 7 liters, or 7 kilos (about 15.4 pounds) per week. Plus back up in case of dealy etc. for my last trip that thus resulted in 30 liters or a full big sized duffle bag and half a carry on. Another half carry on for my feeding pumps, another half for my powerchair battery charger, and a last half carry on for medical stuff that can take baggage transport and can easily be replaced in case of like cathing bags, bandaging material, you name it.
At the moment I'm on about 500 tablets a week, combined with some patches, liquid meds, powdered meds etc. What I do to safe space? Smallest possible packaging. So bottles sized to fit 30 small pills will be used for those pills that are only despenced in bottles and I need in 30 or powers of 30 on that trip. Some meds can be ordered in strips instead of bottles, which for trips I then do. For me it stores easier in the system beneath than bottling and makes it easier for me to safely prepackage one or multiple dosages to take with me where need be.
Tablets in boxes and strips -> strips out of the boxes, strips in ziplock bags and one box and user info are folded flat. Per medication one box comes along, rest goes in the bin. Boxes and info guides go into their own ziplock bags, resulting in only one for all that. Tablet strips in ziplock bags allow me to package much much more tablets in a smaller volume. When stacking just right I can stock upto 100/200 tablets in a space the same volume of one box (most of them contain only 30 tablets) but in a shape that is easier for me to pack and repack if need be at TSA and CPB. With smaller amounts I used to pack per day, so all meds in the amount per day. But with the amounts I take now I've found it's starting to take up too much space. I do make sure all are strips with preprinted the info on it what is what. Combined with the original boxes in my "paper"ziplock bag and needed paperwork (plenty of narcotics and other high-risk abuse and high-risk for smuggling medications on me) for CPB this way it travels a lot smaller in volume but also by staying within legislation.
I do make one exception with those ziplocks; my medication during the travel + half a day in case of delay. Getting your dosages while in transit and packed up can be a pain, esp. with the amounts I'm on you get lost easily half way remembering what you did take out already and what not. Me needing help from someone else to get my carry ons makes it worse. So this is the one exception; ziplock per intake moment with in that ALL the stuff I need that is prepacked, if need be after cutting off the right amount of tablets (still prepacked) from a full strip. Pills that come in bottle -> have small travelbottles and have pharmacy label them. I put times on each bag, to prevent any risk of confusion with the time difference of international travel. Before travel I slowly day by day shifted intake timings little at a time to not have a shock getting used to Orlando timing, but I do not switch in my mind from Dutch time to Orlando time until the day of departure. These ziplock bags I then carry on me in a small fanny pack.
Already laughing at the image of my caravan in carry on travel? Than now add a powerchair and a manual wheelchair, can't carry even the lightest carry on myself and the show is complete. Oh, and I tend to travel solo where I can. Oops, see I knew I was forgetting something; 2.5 checked suitcases of non spillable, non at risk of theft, and if need be easily replacable medical supplies, aids etc. and about half a suitcase of the normal stuff we women travel with like clothes etc. It's not the lightest way to navigate the airport, but in the end it is the safest way healthwise. A no brainer. And I have to be honest; the looks from fellow passengers, ground and flight crew that haven't read their notes yet, airport security etc......... it almost makes it worth it.

They have a much higher stresslevel because of it.

For me it's just part of reality of life. I've got my parents dropping me off at the airport, airport assistance (read; always at least 2 stafmembers getting a big work out) to move around the airport, DME to WDW, bell services once I hit my resort and from there on it's just every day life again.
What I'm trying to say with all this babbling? Don't focus on the negative. Focus on what is possible. It's new when not used to travelling this way (yet), but you will get the hang of it quick enough. Just like you have the hang of dealing with the medications and possible other healthstuff in normal every day life. And see the humor in it. It is there and can make it a much better experience for all involved. Hint; keep an eye and ear open for frequent flyers. There always tends be more than one on every flight having a very visable and/or audible reaction as soon as they spot anyone with more than "their view of acceptable allowance" and get their pants in a very painfull twist worrying about overhead storage etc. As if that is a real problem as long as you simply board within first half of the flight. Very entertaining to toy with that a bit.

It can even be entertaining for DD on dull moments; playing trains with carry ons (obviously in an area where that would not bother any other waiting passengers).
Being able to juggle is important, but health is even more important. Where possible you can adjust the way you package the meds and type of carry on (for instance sets you can connect so with one hand you can then roll 2 carry ons, or using a rolling bag and a backpack, if DD is young a carry on you can roll and she can sit on etc). Not enough to physically juggle it all? Than that is where assistance is for. It might need some explaining that it is not "just" a situation of a mom not being able to juggle, but a situation of medical stuff resulting in needing some help so do not fear being open about that. Contact your airline for this. Get help to the airport of need be, and use available help options that are there depending on how you want to proceed from MCO to WDW. Tip and voila; you are no longer juggling beyond your capabilities.
And remember; the first time is always the worst. It becomes easier, this is no different.