Copy Data from one workbbok to another by transposing data based on condition

I have a VBA automation to be completed as part of my work. I have to copy data from workbook1 to workbook2 (different workbooks), but the challenge is data needs to be transposed based on criteria, simple transpose is not working as need to check some conditions.Region1,Region2.....will vary so need to paste dynamically.

I am attaching file with structure.

Any help will save me a lot, Thanks in advance for help.

Workbook1:enter image description here

Workbook2: enter image description here

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