That looks like what I got, when I tried to install an old 16 bit (DOS) program on 8.1, 64 bit.
8.1, 64 bit has practically NO backward compatibility at all. However 8.1, 32 bit does and it's quite flexible.
On that first picture (screen shot) I would select compatiblility for Windows XP, SP3 and "Run as Administrator", which is what I do for all my old programs that I've used for years in XP.
It's easy to forget to Click "Apply" before you close that compatibility window, but if you do forget, your new settings will not be saved.
Compatibility Mode - Use in Windows 8