VirtualBox is truly amazing. It's not "smooth" enough for the really computer illiterate, but it's not that difficult. Occasionally, you'll run into some of its limitations. Sometimes it's something that just doesn't work in the virtual machine. Sometimes it's something that you have to bang on, or find the magic incantations by Googling. Some things require the command line interface, and aren't in the GUI.
Once again, "straight out of the box" VirtualBox is amazing and fairly easy to set up. It works really well for the things it works with.
It gets tough when you're wanting to access the actual hardware. For instance, with EncorePro, I'd wonder if it would be able to access the SD card, but apparently that does work, from someone else's report of success.
EncorePro/MS SQL server is such a steaming pile of stuff, that it concerns me, too. It's hard to get it to work on a real Windows PC. This is one place where a virtual machine actually helps because you can make a snapshot of your Windows image, try the install, and then restore the snapshot if you have problems with the SQL install.
Get the free SleepyHead software here
for information on the main alternative to CPAP.
If it's midnight and a DME tells you it's dark outside, go and check it yourself.
I have installed EncorePro on my MacBookPro in a virtual machine (Parallels) running Windows 8.
Then I added myself as a patient to EncorePro and downloaded the data from my SD card. There was a warning about the data not being for an EncorePro patient, but the data downloaded anyway.
So I can confirm that you can install and run EncorePro on a Mac, if you've got a Windows virtual machine installed.
And I can confirm that Parallels recognized the SD card and allowed me to choose whether to access it from the Mac operating system or the Windows. I chose Windows and EncorePro got the data just fine.
Also, I made a donation to JediMark to say 'thanks' and to encourage him towards making SleepyHead work for DreamStation data.
I'm running EncorePro on an iPad using Parallels and Windows 10 Home edition. EncorePro reads my data card using the iPad's built in SD card reader.