Thanks for your response! I figured the rocking to sleep would cause him to not be able to resettle when he does wake up, but I didn't think it would cause him to wake up. A few nights he's woken up twice, most nights it's like 4-6 times, and I don't know what I did differently those nights. We do have to work on the rocking to sleep and were going at it really well until teeth/sickness hit. My problem is I run a business from home so nap time is the only time I have to work on my very busy shop, so I've been very selfish and just put him down the fastest way possible. This week son 1 is home from school so I can't get any work done anyways, so we plan to work on the rocking to sleep part.
I did a few searches and read some posts from other people. He is beyond stimulated when he goes to bed!! We never did a wind down routine with son 1 because it didn't matter to him, so I just never started doing one with son 2. He is literally sitting at the dinner table at 5:50 shoving food in his mouth while son 1 runs around yelling, and then dad walks in and says hi and throws him in the air a few times and I run him upstairs, feed him and rock him to sleep starting at 6:05. It's honestly crazy now that I think of it, haha. It never really occurred to me (even though every book tells you not to do that).
We'll work with bedtime (because I do think he's overtired) and I'll try to do a long, calm wind down routine. And see how that works. Thanks!!