i did this with my first son because he would ALWAYS go to sleep on the boob and we could have a lovely cuddle just before i transfered him into bed. we even had low key music i used to play whilst i fed him to sleep.
the thing was, i realised that that was the ONLY way he knew how to get to sleep and i knew that i would be back to work part time when he was 8 months old. i didn't want it to be strangers teaching my ds how to get to sleep as i knew that i could be more patient with him than anyone so we changed the routine. first at bedtime when i knew he was already tired. i would give him his last feed before his bath and his daddy would bath him and put him to bed. at first he HATED our new plan but he got used to it soon enough and now goes to bed pretty well most of the time. you CAN teach them how to settle themselves, its just a lot harder initially than going with the flow.
if you continue to go with the flow, you have to know that that is a potential hurdle coming up (and it need not be daycare, it could be as simple as wanting to leave him with grandparents, daddy etc once in a blue moon and knowing it won't be sad as he can't sleep.)
for me, knowing that i wasn't the only person who could put our ds to sleep outweighed my love of our cuddle time and made me feel more secure about his life.
hth!