2 Transit Gateway and 2 VPCs in daisy chain setup

Without knowing your full topology it is difficult to advice. In general VPC does not support transitive routing so you can not route to another VPC from a source VPC where the Source is not in the VPC itself.

A couple of other options as below would work:

        VPC1
         / 
DX-->TGW1
         \
        VPC2

Or

    VPC1                  VPC2   
      |                    |
DX-->TGW1  <--Peering --> TGW2

Also, any specific reason you are using 2 TransitGateways in 1 region?

Typically you would use only 1 TGW in 1 region; see below 2 statements from the TGW best practices document:

• You do not need additional transit gateways for high availability, because transit gateways are highly available by design.
• For redundancy, use a single Transit Gateway in each Region for disaster recovery.

Yes, this will work but as per the answer from Tushar_J there's normally no good reason for doing this. Primarily it introduces extra costs - the attachment to the VPC and the data processing charges are doubled because traffic passes through both Transit Gateways.

Purely on technical ground. Yes it will work. This scenario can occur in merger/acquisitions. What Tushar is saying is VPC Peering limitation. In your design there is no VPC peering involved.

Please accept answer if it helped.