Jackson's behavior may be related to the fact that he can now get out of bed when he wakes in the night, and something about that freedom is a little scary in the night. Yet, as you said, he chose it. One of his first lessons in getting what you want and finding it not what you thought!! Safety is always the first issue, and if Jackson was still safe in his crib (not going over the top), he could have stayed there for awhile. If you still have the crib up and can try that for a night and see if first he will lay down there, and second if he rediscovers his security, then you will have found the solution you're looking for. If Jackson will have nothing to do with the crib, then next best would be to have a way to lie down in his room if/when he wakes at night, so both of you can sleep. You will be getting up with a new baby, and getting up at night probably for years, so just make it as manageable as possible for everyone. This will pass. Jackson will eventually sleep in his toddler bed, without waking in the night. I would not suggest just letting him cry it out, that way no one sleeps, and is a little like torture to lie there and listen. Remember sleep is the objective, not control. Just my opinion. LOL.
A little about me: I am a mom and grandmom, with children from 27-8 and grands that are 2, AND 1.