My advice is to rehome the dog to a home that has the time to provide the dog with it's needs. Dogs, especially a breed like a lab, needs to have ample amount of exercise. A tired dog is a happy (and non destructive) dog. You will not break the destructive habit unless the dog has another outlet to release its energy.
Knowing you, you are going to take this the wrong way but it's not meant to be, a dog with yours and your roomie's schedule is not a good fit. If I remember correctly from previous posts, it's your roomie's dog not yours? So it would be your roomie's decision. You can crate for extended times, but a younger dog needs the exercise time end of story. And if you don't want to trust the words of people on the forum, just google it, it is a well known fact.
I have had my lab since she was 6 months old and she is 11 now and still has a ton of energy. Coincidentally I got her from an older couple who owned her parents and didn't have time to take care of an energetic puppy. Although because she is older, she doesn't mind the extended alone time (she is alone with my other dog, an 8 year old shih-tzu and my 2 year old cat for about 12-13 hours during the daytime) Again though, these are older dogs so their needs are different.
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