Upgrade to server 2012 questions

I am sure all of these questions have been asked but I am a little pressed for time by a purchase deadline and was hoping to confirm a few things.

Migrating from Server 2008 (not R2) to Server 2012 Essentials. Plan is to host 2012 Essentials as a VM in Hyper-V on a new server running Server 2012 R2 standard. Would like to do this as an in place upgrade if possible.

Questions:

Is it possible to do an in place upgrade from Server 2008 to Server 2012 Essentials R2? I have been told yes but haven't be able to confirm that.

Can I transfer our 2008 user CALS to Server 2012 if we do an in place upgrade? I have been told yes but that is not my understanding.

Plan is to purchase Server 2012 Standard R2, install it as Hyper-V host then use included license to install Server 2012 Essentials as VM. I understand Essentials can be installed as a role from Server 2012 Standard. Any problem here?

Does server 2012 Essential user CAL model apply in this scenario? 25 user CAL limit will probably cover our current needs but we have something like 50 server 2008 user CALS that I would like to transfer if at all possible to cover future growth.

I need to make the purchase today and was hoping to get some feedback on these items to avoid and problems. Thanks
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pmckenna11Asked:
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Cliff GaliherCommented:
You probably aren't going to like these answers. But...

No, you cannot in-place upgrade.

No, 2008 CALs do not cover access to 2012 servers. You'll need 2012 CALs.

The essentials features are indeed a role that can be enabled on 2012 R2 Standard ir Datacenter. No problems there.

The 25 users that the essentials SKU allows are not CALs and are also not a benefit of the essentials role on standard. If you go the route of using standard and enabling that role, you are still bound by the standard licensing, not the essentials licensing. Thus no free user count. You need 2012 CALs for every user (or device, if you prefer the device model.)

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pmckenna11Author Commented:
Thanks so much! What you have outlined above is how I originally understood things.

Just to be doubly sure, even if I keep the same domain once I have upgraded to server 2012 I will need 2012 user CALS? I was told keeping the domain would allow me to reuse 2008 user CALS but not 2008 device CALS. I didn't think this was correct but wanted to make sure.

No free lunch......
Cliff GaliherCommented:
CALs have nothing to do with whether you keep a domain or not. They grant permissions to access a specific version (or older) of a server. So, no, there is no way to access a 2012 licensed server with 2008 CALs.
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