I have checked in many a cabin sized piece of luggage and never noticed them being handled any different from bigger sized items.
At times I have chatted with the check-in staff when checking in a small case, they always reacted in a way that suggested that it is often done.
They do understand the need when you are having two pieces when only one is allowed for carry-on or when you mention carrying items not allowed in the cabin.
Looking out of the plane to the luggage carts on the tarmac you see all sizes of luggage mixed and when they put in the belly of the plane one by one, they are thrown no more gently nor more wildly than the bigger pieces of luggage.
On reclaiming luggage, the smaller items are, again, mixed with the bigger pieces and come the normal way.
So make sure your cabin allowed trolley is sturdy enough to handle normal luggage handling.
In all cases of luggage damage, get to the location within the luggage reclaim area where you are going to be helped when luggage is missing. Often the same location as where you collect out-sized luggage, but it can also be a different office off the main hall or a glass walled one in the hall.
Get forms filled out and photos taken (if only by yourself if they do not do it as well) and do not leave till you have been seen by staff.
Claiming online or by mail after you come home is not as likely to be successfull, as they can easily claim you have damaged the case since or have substituded a damaged case for the one you used.
But I have always taken sending in luggage as taking a risk. If it breaks in a predictable way, I replace it.
I might take action if a new strong trolley is broken or ripped open, but a small dent or even a broken off wheel on a used one, bad luck.
In some airports you can get your luggage plastic wrapped. In some you can get sturdy plastic bags that encase your whole luggage (mostly for backpacks but if you see them supplied you can ask.)
And you can of course buy a bigger case or bag and put it outside your cabin sized trolley.