Within weeks Tommy claimed the crate as his own space. He learned quickly that it was the one place that was all for him, nobody would bug him when he was in there. To this day it's HIS - if there's too much going on, if he isn't feeling well, if he's tired or just wants some time by himself because we're annoying him he goes in there. I don't lock him in anymore during the day, we've left him out for the last few months, but nine times out of ten he spends his time snoozing in his crate anyway. Everybody I know was against crate training when we got him, but now that they see how much he loves his space they've changed their minds.
The dog walker is a great thing, he'll love that!
My only advice is to stop feeling bad... you're a great doggy parent, you're doing everything you can! If you feel bad putting him in there, then he'll sense that from you. I used to just find a treat that Tommy thought was irresistible, and then the only time he got it was when he went into his crate by himself. I'd say 'kennel', and hold the treat part way in the crate, and he learned reallllllllly fast that 'kennel' means 'go in there and get the really good stuff that she holds out on the rest of the time', LOL.
It DOES get easier, and you're doing really well