OK I know some people might be horrified at this... I’ll just give you the background first. My DS and DD share a room, DD is great at going to sleep by herself but she needs the door closed so it’s nice and dark and quiet. DS is mostly ready to go to sleep after DD and he needs us to help him go to sleep and he must have the door open. So it just doesn’t work. As soon as we try to put DS to bed he wakes DD up. Our solution is that we just let DS fall asleep on the lounge with us and carry him to bed when he’s out to it. They both mostly sleep through the night and if they wake we don’t have too much trouble settling them again. There’s always a bit of random co-sleeping going on with either one (or both) of them at times as well. Neither of them have a set bed time because when they get tired really depends on how much sleep (if any) they’ve had during the day. I say horrified because I know some people will think that letting you child fall asleep on the lounge every night is just stupid. But we’ve tried other things and this is just what is by far the most calm, peaceful, functional way of dealing with different bedtimes, different going to sleep needs and DS + DD sharing a room for us as a family.
Believe me Rach, I've considered letting him watch tv in the loungeroom until he falls asleep - less whinging that way.. and we have done it on occasion, just to stop the arguments.
We do walk out if he's stuffing around, and he just comes out, and then tells us that he needs one of us to fall asleep with him, but then we go in there, and he won't even TRY to go to sleep - thats what makes us furious, that he doesn't even TRY to go to sleep. Just lays there with his eyes open.. arghhh!!!
He doesn't have day naps anymore, not since he was 2. He sometimes falls asleep in the car for about 10 minutes, but he's a nightmare to get to bed, whether he has had that time or not.
Anyone want to adopt a 3.5 year old? He's smart - just not very obedient...
Mel the first few times we did it (let DS fall asleep on the lounge) were out of sheer, exasperated exhaustion. Our situation was pretty much exactly what your's is now. But now were all addicted and wouldn’t have it any other way. DS and DH play and talk together, everything is so peaceful. I’m free to potter around doing washing, cleaning the kitchen (and BB too of course) and DD’s sleep is uninterrupted. But I still feel really weird, like I’m confessing to doing something bad, even though I know it’s not. It’s calm, it’s peaceful and it works for us. Anyway, I just wanted to share my experience with you. I probably haven’t helped at all though.
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the first few times we did it (let DS fall asleep on the lounge) were out of sheer, exasperated exhaustion. Our situation was pretty much exactly what your's is now. But now were all addicted and wouldn’t have it any other way. 
DS and DH play and talk together, everything is so peaceful. I’m free to potter around doing washing, cleaning the kitchen (and BB too of course) and DD’s sleep is uninterrupted. But I still feel really weird, like I’m confessing to doing something bad, even though I know it’s not. It’s calm, it’s peaceful and it works for us. Anyway, I just wanted to share my experience with you. I probably haven’t helped at all though. 
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