Not sleeping well AGAIN

Hudson has never really been a great sleeper. We got a period of time where he wasn't teething that he would sleep from 9PM-7AM. We felt so lucky on those days. Right before my spring break we took Hudson to the circus. We don't know if it was the circus (clowns) or just his age and having separation anxiety but he definitely is having trouble sleeping AGAIN. I even bought him this bedtime turtle that is a plush with a plastic shell and the shell has cutouts in it that projects stars and a moon on his ceiling. It has seemed to help with him going to bed. At one point, he cried a couple nights for almost 2 hours. We always go in after 30 minutes and hug him and tell him it is ok then leave. Now we are getting him down easily but he is waking up on the dot almost every night around 230-3. One of us will get up with him and take him downstairs. It might not be the best solution but we both need alot of sleep and we just can't stand to hear him cry for an hour or so at night during the week. I think this is going to have to be my summer project while I am off work. We also may need to consider switching him to a toddler bed. Just not sure at this point what is the best option but we are doing what is best for our family at the moment. We love our little guy so much!