My brother has the same problem. He cannot have dental work done because he has very weak bones in his jaw...so he has lost a lot of his teeth....I take whatever we are having for dinner and put it in a food processor and chop to a fine texture.....it has all the flavor...just already in tiny pieces. When I fix a roast, I put the meat in, chop, add gravy on his plate with mash potatoes and I also chop the carrots in the food processor. Be sure to add butter and seasoning to the dishes. Deserts are pudding with vanilla wavers in the pudding so they are soft. My bother, too is a diabetic, so I fix a lot of suger free jello with whipping cream poured over it with no sugar in the cream...he loves the taste anyway. I also use whipping cream and crumbled chocolate cake mixed together. After all, it is about taste even if it doesn't look great. So cooked turkey, ground up put on top of cornbread dressing (with lots of chicken broth to make mush) and gravy on top.
Cranberry sauce....you can make this sugar free...with sweetner after you cook the cranberries and run through the processor. Best wishes to your family.