If this precise look is a requirement, I invite you to consider our Magic Reporting solution, with which we could tailor to suit, and you could then run in real time from a dashboard right within Workfront. Happy to chat further offline via firstname.lastname@example.org if you're interested.
On the other hand, if you're willing to compromise the look, I'd suggest you create a Task Report in matrix mode, grouped by the Portfolio and Project horizontally, then by the Planned Start Date (to the month) vertically, filtered to Task Number = 1 (the first task, assuming each project has one). That should at least give you a checkerboard of the information, which you might then be able to fuss with (e.g. coloring the cells) to get it in the ballpark.