If your app or game does not work, the first thing you should do is check out https://appdb.winehq.org/. If you can find your app or game on there, it should give some hints that might be useful. If it does not work on Wine then there is a good chance it won't work on Boxedwine either.
If the game/app was made before 2000, often changing the Windows version that Boxedwine will report to the game can help. Set it to Windows 98.
Some older DirectDraw games, like Diablo and Starcraft, might not draw Windows common controls correctly or perhaps not at all. Checking the box on the container options for "DD GDI Renderer" could help. This option will have no affect on Direct3D and OpenGL games.