Mocha had the same seperation issues when he was younger. He would whine and cry like no tomorrow whenever he was left alone. You just have to learn to let go and realize that they eventually get over it. I too, suggest leaving him for increased intervals of time. I know it's hard, but you can't give into his whining/crying. If I had always given into Mocha's crying, we would be nowhere by now. But now, I can leave him home all day if I need to. I bought a Pet Cam so I could see what he does when I'm gone...and lo and behold he just sleeps during the whole time