Sounds like anxiety to me. I had this issue with a 3 year old and what worked for me was a picture schedule. Basically make a visual schedule of your day, you can print the pictures from online. Kids have no concept of time and coming from a chaotic home with no structure means this child feels afraid.
When he comes to your home you can take a few minutes to go over the schedule and then post it where he can see it. This way he knows that mommy comes after X Y Z.

As for asking you a hundred times that is part of the anxiety. Maybe get some books about feeling sad or missing their parent and name the feelings. Then say “Timmy I already answered your question, I am not answering it anymore. What does your schedule say, what’s coming next” to get him refocused.

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