I'm sorry that Skylar has that. It does make us feel really bad to hear them crying when we leave. Rudy had that also. I tried a lot of things to help him with that and the only thing that worked was getting another dog.
Now when I leave for work, there is not a peep out of Rudy cause he knows that Lucky is right beside him in another crate. I know you said it's not the best time to spend money right now, but I do hope something helps for you and Skylar.
Let us know.