Currently the Strategy --> Initiative screen is totally manual. You just drag and drop initiatives to where you think they should go in terms of value and estimates and it totally does not take into account the value and effort estimates that are applied to the features underneath those initiatives. If this was done it would give a great visual on effort vs value.
It's possible to create pivot and timeline reports to analyze which initiatives have the highest Aha! scores.
This can be set up in a pivot table by show Feature name as the row, Initiative name in the columns and Feature scores in the Cells. By sum values, you can see the total summed Aha! scores across each initiative.
The Strategy roadmap screen is meant to be used to outline the strategic roadmap. You can also apply various filters to analyze initiatives by status.
We would suggest the workaround noted above to analyze initiatives. However, we are unlikely to make additional updates in this area based on current priorities, community feedback and current functionality. We hope you can understand.