The 5.0.x series have no problem installing on the 10.8.5 VM. 5.1.0b1 and b2 never finished the installation. There is also no problem installing on a 10.9.5 or a 10.10.x or a 10.11.x installation (VMs of course, all of them).
The installation stops at the "postflight" script (I can provide installer logs or comparisons if needed), but the source directories that are responsible for creating the installers (VirtualBox-5.x.y/src/VBox/Installer/darwin) are the same except the "Makefile.kmk".
The installer's first error appears to be:
Code: Select all
Jun 7 12:11:52 10.0.5.15 installd[538]: ./postflight: /Library/Application Support/VirtualBox/VBoxDrv.kext failed to load - (libkern/kext) link error; check the system/kernel logs for errors or try kextutil(8).