Hi Mum2Willie. Yep I have been there and good on you for creating such a comforting sleep environment for your bub. It is likely to make the transition easier. A book to recommend is Pinky McKays "sleeping like a baby".

But some notes from me...
1. Just try putting your baby down after a cuddle but before he actually goes to sleep. Sometimes I haven't tried because I don't think DS can do it and then when I do I am pleasantly surprised. The worst thing that can happen is that he gets upset and you pick him up again. Make sure he has any comfort items that he is used to for the transition.
2. Make sure your DS spend some happy time in his cot when he is awake. This will mean he is much more comfortable in there when he is going to sleep and also when he wakes up.
3. Try to transition when other things aren't happening. eg. don't also try and move him into a different room, or don't try it when he is teething or sick etc.
4. Put something on the roof that is interesting but not stimulating. It will give him something to look at as he is drifting off. The ceiling fan is great for DS but we live in a hot climate as well.
5. Have some quiet but steady background noise while he is drifting off as it reminds them that you are around and they are not alone.
6. Don't fret too much. Daycare carers are used to bubs getting to sleep in lots of different ways and they don't seem to fight sleep as much when they don't have their parents around - probably because they stay awake until they are really tired with all of the activity and also because they don't have as strong a desire to remain with the carer as with you.

Good luck and keep us updated!