Okay--the little man is out for the night! Thank goodness (we're dealing with molars

).
First of all, I'm happy to hear that he did a long stretch last night. Woohoo! On the flip side, though, I think there are some things that still need to be tackled--and we need to get a bit tougher, considering his age bc the longer he has habits, the harder it will be to get rid of them. I also think the key to more good nights and no EWs is getting his days figured out.
I still cant put my finger on it, I'm not sure what it is thats waking him up. His teeth were bothering him last week but not any more. Could it be that he needs a diaper change? I have never really changed his diaper at night for a while now, but in the morning it is really full. Or is it that he is UT? He's doing two long naps, in the AM and PM.
It's kind of hard to tell whether his nights are OT or UT, tbh. It looks like his A times are either too short or too long, and he's getting a lot of daytime sleep on top of that. When that happens, night sleep can be affected and can lead to EWs (yup, EWs can be either OT or UT). I don't think he needs a diaper change, tbh, unless he's leaking through his diaper. If not, I'd leave him be so that you've cut out any stimulation that you can during the NWs, iykwim.
His morning A is 3h15 give n take, the second A is really short, sometimes he's sleepy after an A of 2h, usually only 2h30. The third A is 3h30 or 3h45. In case he is UT, should I cut the AM or PM nap?
You mentioned that you have to help him transition during his first nap. You shouldn't have to at this age. He should be able to take long naps on his own. How long into his nap does he wake up? Are you in his room when he does? What if you were to just leave him to resettle?
I'm wondering if he's now ready to push that first A time out a bit more, say, to 3h25-30. The second A time is really too short for his age. Yes, it's true that not all A times have to be the same length; but a 45 minute difference is too wide a swing, I think. Sometimes babies can act sleepy out of habit, especially at this age. If that's the time he's always had a nap, then he'll probably be more inclined to show sleepy cues then. Granted, he takes a long nap; but I wonder if he could do a touch more...say, ~3h (and we can up this after a few days if needed).
I think his last A time is too long for him just yet, and that's why he's waking at night. I know it's longer so that he can get to bed at a later time. I think by extending the previous 2 A times, that last one will be closer to the others and his whole day will be more in-line. So, tomorrow, how about trying something like this (adjust wake-up time to his):
Awake at 6
E: bottle, solids 1h later
A: 3h30
S: 9:30-11 (1.5h)
E: bottle, solids 1h later
A: 3h
S: 2-3:30 (1.5h)
E: however you do your late afternoon/evening feeds
A: 3h30
S: bedtime at 7
So, that's an overall day of ~13h, which is fairly long. I wouldn't really go longer than this right now. Also, I have a feeling that he'll need the second A time pushed out a bit more in the coming days, but for the next 2-3 days, try that above routine (remember, it doesn't have to be exactly on the dot, timing-wise, but a 15 min or so sway is okay). If you could keep track and have your nanny keep track of his EAS for the next 2-3 days, that would be great so that we can have something to look back on.

Its just the naps that I still rock him. I know its not right, but I'm waiting for his 2-1 transition before I try to get him to sleep independently for naps, since I will have to only do it once a day and not twice!
To be honest, I wouldn't wait for this. I'd tackle the independent sleeping now while he's still young. Sure, it might be hard for a few days, but I can guarantee you that when you can just lay him down and leave the room, it's the best feeling in the world! We weaned DS's swaddle at ~6.5 months, and it was rough for 3 days, but very worth it. Now I know that when I need to APOP a nap or two, it won't upset the apple cart

I bet it will be easier than you think

And it's mainly about you being mentally prepared to go through with it.
And while we're on the topic of the 2-1 transition, it's actually a very gradual process that can take months to happen. For some babies, it starts off with them refusing to nap after a certain time of the day (sounds like what Emma went through). For others (like me), A times got too high to have 2 x 1.5h naps, so we had to start cutting back on sleep. There are 2 approaches (usually) to this. One is the short AM/long PM; the other is the long AM/short PM. It all depends on the LO. In either case, A times need to be up ~5h each to handle dropping to 1 nap. So, I think your LO has a long ways to go yet with this

But, once we get his days figured out, it may be that he does need less daytime sleep--but let's cross that bridge when we get to it

So, let me know what you think about all of this. I know it's a lot, but Emma and I are here for you to help you through! Really, you should be proud of yourself for how far you've come! I'm am so happy that you're feeling better, too. That is so important! *hugs*