
Hi jayj,
Firstly, feed ALL meals in the crate with the door closed over while eating and re-open when finished. During the course of the day give the puppy treats thrown into the crate (don't worry if he just goes in to collect them and brings them out, as initially all you're aiming for the association with a crate is to have absolutely NO adverse /negative associations). When the puppy is sleeping or almost asleep, lift him gently into the crate.
In the evening, while you're watching TV or whatever, make the crate as den like as possible - cover over with a blanket or duvet so that all three sides and roof are filled in and only the entrance door and panel are open. Put something in the crate that smells strongly of you such as a sweater, or a tee-shirt etc. and give the puppy in a toy plus his evening meals.
When you're going to bed IME it is better to put the puppy in the crate and have it near your bed if that is where you intend for him to continue sleeping. If you decide he would be better downstairs or on the landing for example, you can gradually move the crate out of the bedroom or alternatively sleep downstairs on the sofa for a few nights until he finds the crate to be his preferred place/sanctuary. I'd try and develop a routine of say last time out for a wee before retiring around midnight, pop puppy into crate with his toy, your item of clothing and a safe chew and then lights out. Get up around 4-5 hours later, preferably before he wakes first, and take him back out for the toilet - no fuss, just a loo stop and back into his nice snug crate.
Never use the crate as a form of punishment - he should grow to see it as his personal safe haven when you're not around so positive experiences are essential :)
If you follow the above steps carefully and patiently he should quite quickly adapt to the crate so that you can have a little peace of mind during absences or over night that he can't hurt himself chewing wires for example. IMO pups should never be allowed to howl or become distressed, with or without a crate, and if crate training (or any overnight training even without a crate) is done properly and consistently then the puppy wont get distressed in the first place :)
HTH, good luck Teri