To allways keep JRiver on top would be kind of frustrating for users trying to access other apps. So it's not the best idea imo.
You could easily create some batch files to launch the programs on startup. I don't remember the exact code, but it would go something like this. Check the syntax and do some googling if it do not work.
@ECHO OFF
C:\Program Files (x86)\powerstrip\powerstrip.exe
TIMEOUT /T 10
C:\Program Files (x86)\J River\Media Center 19\Media Center 19.exeCreate a StartApps.bat file with this content. Create a Scheduled task under Control Panel. Give it a name, make sure the "Hidden" check box is selected. Set the Trigger as "At Log On" and action to "Run Program" and point it to the batch file. That should launch the Powerstrip 10 seconds prior to JRiver MC.
I can't guarantee anything though. Don't have the time to test it now