Help with techniques on how to populate tables in different months Formula , VBA or Pivot?

Hi all,

Just made an account on the forum as I'm completely stumped on how to tackle my issue. Basically I'm looking for a way to scan through the Data dump (Sheet2).Filter through what milestone falls into the correct month criteria i.e the next three months then correctly populate each cell in the column with info.I am a complete Excel Novice so my ability and understanding is very limited, perhaps there could be a way through VBA or pivot table?
Also the formatting on the tables would have to be altered accordingly i.e if there is more in that certain month then the rows have to be extended or if less then reduced.

I've attached an example of what my issue is , if someone could take sometime to have a look that would be hugely appreciated

Thanks in Advance all !