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Hello.
I think if the CIDRs overlap, you will probably not be able to communicate.
https://aws.amazon.com/transit-gateway/faqs/?nc1=h_ls
Q: Can I connect Amazon VPCs with identical CIDRs?
AWS Transit Gateway doesn’t support routing between Amazon VPCs with identical CIDRs. If you attach a new Amazon VPC that has a CIDR which is identical to an already attached Amazon VPC, AWS Transit Gateway will not propagate the new Amazon VPC route into the AWS Transit Gateway route table.
So, I thought that if I were going to do it, I could solve it by setting up PrivateLink and using it like a NAT.
https://docs.aws.amazon.com/vpc/latest/privatelink/what-is-privatelink.html
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In shameless self-promotion, here's some more information: https://aws.amazon.com/blogs/networking-and-content-delivery/connecting-networks-with-overlapping-ip-ranges/