D.B.
There's a great book recommend by tons of moms on here...Healthy Sleep Habits, Happy Child
http://www.amazon.com/Healthy-Sleep-Habits-Happy-Child/dp...
Its a good read and you don't have to do front to back..you can read the beginning and then go to right age section.
I have two kids - just turned 2 and other is 11 months. First one sleeps like a perfect angel...2nd is a different story. Routines are essential. About 30 minutes before you want him to go to bed - do bath (wash, dry, lotion), then read books with only a night light or lamp on, then maybe sing or nurse. Try to nurse but not let him fall asleep in your arms - get drowsy but not completely asleep and then put him in bed. Do all this in that 30 minutes. If you take longs baths like we do then maybe start 45 minutes. Once you put him in bed, you really should stay out of the room which might entail some nights of crying. If you can battle thru about a week of that you might have it made. If not, then you can choose to go back in and soothe him without picking him up. Maybe lay him back down and rub his back and just say some key terms "its night night time I love you". As for who is involved it is up to you. My hsuband and I both do bath time but we have two kids. We read soem books all together then we seperate into their rooms (one with each kid). You can do it all together or maybe you do bath and Dad does books. Ya'll decide on your schedules. You might even try a timer for the 30-45 minutes so you and your hubby stick to the routine and your son might also enjoy that...he'll learn quickly that "ding" time means night night. Also try to pick the same books to read each night or sing the same songs. that all helps and gives comfort to them. It might get boring to you to read the same ones over and over, but let's say you read 3 - let him pick 1 or 2 andthe last one always be the same.
I know this is long but I hope it helps. I agree with your hsuband that if you get bed time down naps might follow along. He's in that transition stage but one nap is probably good enough as long as its long (like 2 hours) maybe from 12-2.
Good Schedule which always worked for us and many of my friends:
7AM - wake & play a little
7:30AM - breakfast
8-10AM playtime
10AM snack
10:30-11:30 playtime
11:30 lunch
12-2 NAP TIME
2-4 play time
4PM snack
6PM - dinner
7:15 bath / bed routine
8:00 IN BED for NIGHT
Last since he has the roam of his room I'm not sure about that one...can you gate the playroom off JUST at night? This way if he gets up he can't really "play" and not sleep if you let him cry. If you don't let him cry then you don't have to gate you could just keep putting him back in bed and do the soothing.
Good luck...feel free to send me a message anytime!!
ps...another great great book is Parenting with Love and Logic. If you start now you'll never have ANY problems with discipline (promise!) including bed routines...its the best!!