I had these same issues, until I changed the partition type
in the master partition table, by mounting the hard disk
image into a Linux VM, and using fdisk. Then HDMAINT
had no problem making the partition, and PIP worked fine,
it seems to STAT as expected, and the programs execute.
I use only VirtualBox for these kind of things (after some
bad experiences with VMware Fusion upgrades breaking
my Linux VMs, so I don't use VMware for anything but my
Windows VMs now).
There's a working set of goods on my web site, here;
http://www.hytherion.com/beattidp/comput/cpm86/
This is CPM-86 booting to a 4MB hard drive -- please feel free
to use it as a working example, and do let me know if somebody
builds a fully-loaded development system (even with GEM etc.).
Note that it was created using the latest version of VirtualBox,
version 4.2.6, running on Mac OS X.