Thank you for all the wonderful comments on my desperation filled post from last night! The suggestions were varied and gave me a lot to think about; I really appreciate all the helpful thoughtful comments and the supportive ones, too.
Hearing things from other's perspective gave me a lot to think about, and helped me solidify what I think is the best plan for us. Well, as much as you can ever solidify a plan when children are involved.
I think many of you were right about Finn's naps. I don't think he's ready to give them up, but it's time to start shortening them. He currently naps anywhere from 2-3 hours; Nanny M always wakes him up if he's still asleep at 3. She's going to change that to waking him up at 2:30, and then gradually change that to 2, so he's not napping more than an hour. I think he does need a short nap; he gets really drowsy if I keep him awake, and actually goes to sleep easier for his naps than he does at bedtime.
The only sleep book I've read is the No Cry Sleep Solution. And even that wasn't helpful at first - my problem has always been getting Finn to go to sleep. Once he's asleep, it's rare that he wakes up in the middle of the night and won't go back to sleep. But the part I use now is the section where she talks about transitioning from needing a parent in the room to fall asleep to being able to fall asleep on their own.
So when I switched to the toddler bed, it was with that in mind. Our first few weeks in the toddler bed were ok (after the first night). Our bedtime routine of stories and pjs is about 30 minutes - he hates getting his pjs on, but it works well if I let him run around naked for a little bit, and then bribe him with books. Then at 8pm, I would rock him for 5-10 minutes, then put him in his bed. At first I sat next to the bed, and he'd eventually fall asleep. It might take 45 minutes to happen, though. I was gradually working my way away from the bed, as suggested in the book, but I think I moved too fast. And that's when he started trying to get out of bed.
I don't want to move him back to the crib because I think that's moving too far backwards. I couldn't put him awake in the crib and then sit next to it or even in the room without screaming. And while I know there's a good chance that crying is going to be required to get our sleep fixed, I don't think I can handle that degree of crying. And despite the awfulness of getting him to go to sleep, I'm actually getting much better sleep than I have in ages, because he comes to me when he wakes up. All I have to do is lean over, help him in my bed and go right back to sleep. I really enjoy cosleeping still, but I really enjoy my time in my bed without him, too. So the half the night in his bed and half the night in mine is perfect for me right now. I'll work on breaking him of that habit later, if it doesn't taper off on its own, as I suspect it will.
I thought about Simone's comment, that Finn isn't being a problem, he has a problem he needs my help with. And Jen and Tiara's comments about teething and growth spurts. And I realized that this week Finn's footie pjs are suddenly too tight and he's constantly chewing on his sippy cup straws. And the fact that I just went out of town and left him for the first time ever. Which makes me think this past week has just been the perfect storm of absolute crap sleep.
It's pretty clear that Finn doesn't want to fall asleep on his own - he wants me to be close by when he does. He can put himself to sleep if he wakes up in the middle of the night, but maybe he's also having trouble figuring out how to go to sleep at the start of the night. And he's probably not quite tired enough.
So, in addition to shorter naps, I'm going to work on getting him completely used to falling asleep in the bed by himself, and then follow the No Cry Sleep Solutions suggestion to very gradually move out the of room, sitting a little further away from the bed every night, until I'm finally out of the room. Which means lots of sitting in his room as he falls asleep. I'm going to start doing some board review then - I'll load some lectures on my phone and watch while I'm waiting for him to fall asleep - which should help me handle my frustration at being stuck in there.
I started tonight by rocking him to sleep, but not to the point that he was sound asleep, just to when his eyes first slid shut. I then put him in his bed. He turned over, grabbed his monkey and was asleep. By 8:25. My parents are going to be here the rest of the week, so I'll probably stick with that the next few days. And then from there will start putting him down when he's drowsy. It'll be a gradual process that will probably take me a few months, instead of the few weeks I was hoping for. And I know at some point I'll have to deal with him crying. But I think if I do things more gradually, he'll have a better understanding of what it is I'm expecting him to do, and it might actually work.
This is probably way more than most of you wanted to know, so if you're still reading, thanks for sticking with me! Any other suggestions that anyone wants to throw my way are very appreciated, even if the suggestion seems completely opposite of what I'm currently planning to do. Toddlers change, and plans change with them, so I'm open to hearing everything.