Migrate Windows Server 2008 to another server

Solution 1:

There is a solution for this.
You can do backup of your existing Win 2008 R2 (over network) and then new install. And when you do new install - you can do recover from backup.
This works across different hardware like a charm.
I've done it at least 10 times.

• Physical to Physical HP Gen6 BL460c to HP Gen8
• Physical to Virtual KVM
• Physical to Virtual VMWare

Have a look at this article where the whole process is explained rather nicely https://technet.microsoft.com/en-us/library/cc755163

You would have to re activate your Windows Product key after this as your hardware changes.

Solution 2:

Migrating between physical servers in the way you're proposing isn't really a thing. Can it be done? Sometimes. It's nearly always quite painful though.

Instead, install a fresh OS on the new server and move services over gradually to the new server until the old one is idle.

In fact, while you're at it, you might as well start using a virtualization layer (either VMware ESXi or Hyper-V), after which you'll never have to deal with difficult migrations in the future.