VMware is overkill, but it's fun.
With VMware you could run BlueIris or iSpy on another VM on another Windows or Linux OS VM, that way if you hate Milestone and want to try something else, you can easily do that.
VMware has a 'snapshot' feature that allows recovery from even the worst OS mistakes; snapshots prevent you having to resinstall the whole OS when an upgrade goes sideways.
If you need to remotely manage a Windows instance, use either Cybelesoft Thinfinity (free HTML5 RDP solution), TeamViewer (free) or GoToMyPC.
Milestone Remote web viewer lets you view/playback video but not manage/control Windows PC or NVR application. I believe you could do that with the SmartClient, but have not tried that.