OP I'm so sorry you feel judged. The only thing I'm judging here is the TSA if they've made you go through this repeatedly when it's not at all required.
I travel alone as a severely disabled person. I am not physically able to carry the bin of my stuff; I can't even stand up from my
scooter for more than about 30 seconds at a time. I can't unload my stuff from the scooter and place it in the bin. I can't put my shoes in the bin because I can't pick them up from the floor.
The TSA will not require a passenger to do stuff they cannot do or that isn't safe. It's illegal. Every time they decide to inspect my laptop or anything else, they carry it over there themselves because I can't. I travel with a soft cooler of refrigerated meds and syringes that gets examined every time, and that I could carry, but the area they bring it to for secondary inspection isn't accessible to my scooter and I can't walk it over there.
There's no such thing as "unless you can pick up and carry your own medical equipment you don't get to pass security." You and your husband can choose to do so if you like, and I'd hope no one would judge you for it. It's just that I have seen many many instances of TSA abusing their power, making up nonexistent regulations, once an agent tried to stick his hand down my pants because he absolutely insisted I had loose change in my pocket, as he could not grasp the concept of a hip replacement on a young girl. I didn't even have a pocket in those pants, btw, they were sweatpants.
If it's your choice, there's nothing wrong with it, but please don't let the TSA push you around or demand you do anything unsafe for yourself or for your equipment.