Hi,
I think Norway has addressed most of your issues. What you may need to be concerned with, even with purchasing of volume licensing from Microsoft, is the hardware issue is not under your direct control, but rather in the control of various "contractors" who many of which you admittedly tell us won't even by on the PC platform (Mac & Linux machines). Microsoft has different licensing issues which need to be looked at when running on non-PC (X86/AMD/VIA) hardware; and even yet more different licensing issues when running VMware or another VM vendor such as Silas with W10 keys. Open licensing and Enterprise licensing is considerably different outside of the US; I worked in companies where we shipped similar configurations (Win2k+VMware) on both Unix & Linux platforms to Europe and Asia. Not sure what "SMB" means, but if it's like a Microsoft Platinum or Gold Partner or a Developer, you'll need to contact Microsoft directly to avoid patent and licensing infringements in your country as Norway mentioned.
You're biggest issue should be that your licensing of W10 keys is "authorized" and "approved" directly by Microsoft Legal Department for use in your country (Australia right?). The best and only way to do this is to contact your local Microsoft Office in your Country (I know you have one down there, as I've talked to them before), and get in touch with your Microsoft Rep in that Office. If you're VMware-W10 deployment is going to involve more than 250 licenses (250 computers with VMware+W10 licensed key installs); you had better be talking to that that Rep prior to shipping or installing any W10 anything. If you are under that number of planned installs, you still need to talk to an MS Rep and you may need to get one assigned to you. This is a process that many folks aren't willing to do, as they don't want an actual MS employee in their "home shop". I've done this for many, many companies over the years, and there is just no way around it, unless you wish to invite litigation on your W10 licensing violations from both the SPA and from Microsoft's legal army (some say they have more lawyers than most countries entire actual army). I myself am not an attoryney, but I've dealt with MS licensing issues going back to 1987 and have never run afoul of MS by doing this. If your scheme is to bypass MS by reusing keys on non-employee hardware, then by all means do so and don't take my advice. That's up to you.
Talk to a MS rep if you have one already, or get one especially if your licensing target is above 250 units, and MS will take care of all the legal mumbo jumbo for your country location, and give you big discount pricing (often better than a Microsoft distributor) for your licenses. As a past member of SPA, I would be remiss not to give you this advice and warning. Be aware also that Microsoft annually changes their infringement suits based on licensing quantities being resold; that 250 unit number was old-from 2001-and they frequently change it. Again your local MS rep can give you current unit quantity levels. Even if you ship less than the 250 units I mention hypothetically, you still stand to gain by dealing directly with MS on the volume licensing of the needed W10 licenses. Things like being able to setup a customer-specific download portal for your licenses through Digital River or similar, that Microsoft can monitor your in use unit count with, or providing you with a custom VMware+W10 keyed license image are things they can do. I also heard recently that MS acquired the VMware folks, and so it would be easy to provide packaged downloads with both already setup for you-for a custom fee. This could also be done through a VAR (Value Added Reseller). We did some similar stuff with our customer VM-based images as I said; and shipped on 3 continents. The discounts can be BIG; we used to buy Win2k+VMware license combos for like $42 per seat through MS; that's almost $100 cheaper per seat than buying retail license keys for $100 a pop plus whatever the per seat VMware license fee is you are currently paying.
Hope that provides some additonal insight. I don't think MS will like your sub-licensing VM scheme however, due to the no-control issue on the hardware ownership, but that's just my opinion. If you fly under their Radar, you may get away with it; as they are quite busy with much larger infringment lawsuits from the big corporations worldwide; they may not come after you--at least not right away.
<<<BIGBEARJEDI>>>
