Hiya Laura!! :hug:
I think if he can go a couple of times for an hour or so before you drop him in the deep end, then that will benefit him, however, I think you have got to be cruel to be kind, maybe Im wrong on this, but I just wouldnt make a fuss of you leaving, dont say bye, things like that, he will soon associate the word bye with you leaving and then he will howl even harder!
See I disagree, to a point you do have to be cruel to be kind, have a routine children love routine its the only way they know whats going to happen next! When you drop him off dont make a fuss set yourself as an example, if mummy crys then he deffinatly will! Hand him over say what you need to say to the minder, give him a kiss say bye bye.....and leave........cry your heart out all the way to work ( as I always did, did it again today as is daughters first day at new school...she is 8 though!!)
If you never say goodbye is can cause trust issues, your kids need to know mummy does go away sometimes but she always comes back! If you sneak off without saying anything they constantly fret if your not in there sight!!
I so sympathise been there and done it and cried my heart out on my way to work everytime!!