chewysmom2005 You say you grew up with rotties, you're experienced with the Rottweiler as a breed
and your mom is a breeder. You have much more knowledge than the average owner about the rotties temperament and what Chewy's strengths and weaknesses are.
Here's a suggestion; Imagine yourself getting a phone call from a stranger giving you all the information you have about Chewy and asking for your advice. What would your response be, particularly regarding his insecurities, crate training and the barking he does when he's behind the gate?
I have a hunch that somewhere during the course of the conversation instead of feeling sorry for Chewy you would be tempted to say;
"look this is a Rottweiler a big dog with a tough constitution; sure he's got problems but many of these problems could by solved with a little training and redirection."
You're the only one that really and truly knows Chewy. If he really can't take correction and re-direction, you'll have to continue to live with it and the consequeces it brings as you've been doing. However if you're making excuses for him because you feel sorry for things that happened in his past, you need to face that too.
To allow him to continue to bark and whine simply because there is a gate between you is only adding to his emotional turmoil... Something no dog needs!
Wouldn't it be more kind to work toward putting an end to his total dependency rather than allow it to contine and even grow?
From the outside looking in; it seems that you're making excuses and letting pity overrule what in your heart you know is best for the dog and as a result you're encouraging his dependency.
Ask the people that know you and Chewy, especially other rottie owners, if they think you're over protective or simply being reasonable.
I have a feeling they'll be more than willing to tell you what they think.
As far as him not eating when you're gone; does it really make a difference, especially since he free feeds? Most dogs only eat when their owners are home; because that's when they're normally fed. Try leaving his food within his reach up on the counter while you're gone. I'll bet he'll eat some then!

Whatever you do I wish you the best, Chewy couldn't have found a more caring home.
