Thank you all for replying. It means a lot. This is such a great site. I took Cobber to see the vet yesterday. After explaining everything that has taken place, our house setup, activities, etc we planned a course of action. A few things were recommended not necessarily in order of importance: spraying the house with Feliway to help calm him, giving him 10 mg daily of Amitritylin, giving him an anitbiotic for a cut he has in his mouth from a tussle while outside yesterday, playing with him more to keep him active and making sure he has enough toys (he already has more than I did as a kid), using coyote urine outside the house to help deter the other cats, not letting him out on our deck anymore and we clipped his nails to save my legs. Its all trial and error, really.

The vet also suggested possibly introducing a kitten into the household which may help keep him active and have a buddy too.

Does anyone else have any suggestions or comments?