Clinger Dilema

We are entering a new phase right now.  I've decided to fondly call this one

THE-SEVERE-SEPARATION-ANXIETY-THAT-WON'T-ALLOW-ANYONE-TO-SLEEP phase.

I'm beginning to lose my mind.

Recently I decided that I was tired of Wy's nighttime bff, Bobo (aka the pacifier).  Having heard from quite a few people that slowly getting rid of it tends to work best, I shifted from letting him have it any time he wanted to only allowing him to have it at nap and bed times.

And that's when the separation anxiety started.

The first week mornings were kind of hard because I would make him ditch bobo as soon as he got up and some days he was just feeling sleepy and crabby so would cry for bobo until we got to the sitters house where he was instantly fine most of the time.

The second week, it evolved into him not wanting me to drop him off, he would cling to my neck and if I did put him on the floor he would bounce up and down, arms stretched up at me, pleading "up up up up up up up!"

During all of this he was starting to get more clingy at bed time too.  It's not unusual for him to stand at his door and cry for a few minutes when I put him to bed.  He really is a kid that thinks he's going to miss something exciting if he goes to sleep when I want him to.  So he whines and cries and stalls, but always ends up closings his door and getting into bed.

At this point though, it's gotten so bad that the second I turn to leave the room he is jumping out of bed and running after me.  I put the baby gate up in his doorway last night so he couldn't follow me down the stairs and he stood and screamed for a good 15 minutes before laying down.

And then he got up 6 times during the night.  SIX!  He was in and out of my bed twice, cried for probably 15-20 minutes when I just ignored him and let him stay in his room, and basically just freaked out all night leaving both of us tired and grumpy this morning.

I'm praying that once his reward gets here we can ditch the bobo for good and start working on some better self soothing.  We have been talking for weeks now about what we are doing with his bobo's now that Wyatt is a big boy.  If you ask him where the bobo's are going he will tell you, "to babies!".  I decided that the best way to deal with it and teach him a good lesson at the same time is to "donate" his bobo's to babies who need them and are feeling sad because they don't have any.  He seems to feel good about being able to help some babies and he's very excited to get his "special toy" to reward him for being such a big boy.

Besides that though I'm at a complete loss for how to help my son feel safe and comfortable on his own lately.  He's always been such an independent kid, there are times when we are home together that he is just not interested in hanging out with him, he would rather play with his toys on his own.  Which doesn't surprise me, I'm very solitary at times, I really value my alone time, so it works for the both of us.

Any suggestions or tricks that I can try?  What has worked well for your kids?