oh it's tough.. but it gets easier... layla still has to be wherever i am... she's 10 months
as for the crate thing.. they gotta cry it out... maybe put a toy in there that he is familiar with... can he see you in bed?? layla had to be put on a chair so she could see me.. .that made it better.. she didn't feel alone... dogs are pack animals.. they sleep together.. so make sure he can see where you are.. also try a heating disk.... it makes layla feel "comfy" good luck we have all been there and are here for you!