Re. On Top,
Sure, I could try to mentally think that I should be on a higher level window when hitting F1, but that extra mental gymnastics doesn't have to be necessary.
The code for MT could be made to know (if it doesn't already) when F1 is selected, and the code already knows when Help is selected from a drop-down within the MT portfolio window, so the code could always force the Help Window to be on top of everything irrespective of which window is active. In that way, the user wouldn't have to think about it at all -- Help would always be on top.
Earnings -- will that issue get fixed?