How do you know the right place for your loved one? How to you know when assisted living isn't enough?

Sorry you are facing this. Assisted living facilities will normally tell you when someone needs too much help and has to go to skilled nursing instead. They will do a functional assessment before admission and actualy not accept the person if they can't manage their care. It may vary from state to state and even -lace to place. Back in PA there was one where they used transfer equipment and were able to take care of my mom for quite some time, even though another facility with the same designation called and told me they could not keep her any more (i.e. gave me the 21 day notice, but we got moved in less than a week.) When we moved Mom to Arkansas, she did some rehab and then skilled nursing, we were not abel to get her to where she could be in assisted living here which required min assist transfers and self-administering meds, which she could not manage. For some people, there may be no place they are ever going to really like, but if you can, try to find a place they do seem to like, where the atmosphere is something they will find pleasant and where they will fit in with the other people. And ideally the person helps pick it from pictures, meeting people there, etc.