Transit Gateway: Connect two DCs via VPN with overlapping CIDR range

I see different use cases here:

1. VPC1 <-> DC1
2. VPC1 <-> DC2
3. VPC2 <-> DC1
4. VPC2 <-> DC2

Separately, use cases 1 and 4 together, or use cases 2 and 3 together are doable by creating two separate route tables for VPCs and have data center CIDRs pointing to VPN attachments.

if you want to do all of them together then the complication arises and you need to NAT DC1 or DC2 (one of them) to something like 192.168.2.0/24 and use that NATed range as destination in the route table. Here the aim is to make one DC's range look different for TGW. This NAT can be done either in Customer Gateway side or AWS by spinning up NAT appliance in a separate VPC then use that as destination for traffic destined to a DC.

With NAT in picture things generally get messy.