Is this round-about migration to SBS2011 from 2008 feasible?

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I run my own consulting software shop,
and I'm currently running SBS 2008 Premium. I'm not utilizing the second server at the
moment, but when I finally get to SBS 2011 Premium I'd like to. The server is already
maxed at 4GB of ram, and I have six drives, one for the C: and the rest are part of a
RAID 5 which is where all user data is stored (Sql dbs, Exchange data, file
shares).

I'd like to get some new
hardware that will eventually run SBS 2011.

My
plan is to get the new hardware which will include disks for a RAID 5 and hardware
virtualization support. I'll then install the second Windows 2008 Server license that
comes with SBS 2008. I'd like to then move the current SBS server from physical hardware
to a virtual on the new secondary server. This is one area I'm not sure of. Is it
possible, and also what about the data on the RAID disks? Will that pose a
problem?

Later when I have enough to buy the
SBS2011, I'd upgrade the secondary 2008 server (running on the new physical hardware),
then setup SBS2011 in a new virtual and migrate from 2008 to
2011.

Would this be a possible route to go? If
not, what would be the best recommendation, given that there will be a delay between
buying the new server hardware and buying the SBS2011
license.

EDIT: I'm planning on using the second
server (not in use at all right now) to install 2008 HyperV on the new hardware, then
pull the physical SBS into a virtual on the new hardware. I've never done a P2V before,
so I'm not sure what to do about the data drive which is currently a RAID5 and where
SBS2008 stores its Exchange data and user folder redirections.

Answer

There is a href="http://technet.microsoft.com/en-us/library/gg490796.aspx" rel="nofollow
noreferrer">migration guide for SBS 2011 which lists the supported
migration path from 2008 to 2011. Basically, href="http://technet.microsoft.com/en-us/library/gg616008.aspx" rel="nofollow
noreferrer">the only supported upgrade option is a fresh install of the SBS
2011 on new hardware in what is called "Upgrade Mode" (it will allow the SBS 2011 server
to join the presently available SBS 2008 domain and pull all Active Directory data) and
the wizard-assisted or manual migration of all data and server software from the old to
the new server.

There is
no in-place upgrade option for the SBS from any previously
installed OS, you always have to deal with a fresh
install.

If you virtualize, this will be not too
much of a concern - you simply fire up a new virtual machine for your SBS 2011
installation. Make sure to get enough RAM for your physical machine - SBS 2011 is quite
memory-hungry, expect a single instance to easily eat 16 GB of
RAM.

I'd like to
then move the current SBS server from physical hardware to a virtual on the new
secondary server. This is one area I'm not sure of. Is it possible, and also what about
the data on the RAID
disks?

The
name for this procedure is "physical-to-virtual" (P2V) conversion.
You would have a different set of tools depending on the virtualization platform you are
going to chose to accomplish this task. For VMWare virtualizaion products (vSphere
ESXi), the VMWare converter is free and really easy to use, you will find a lot of href="http://www.vi-tips.com/2011/11/p2v-with-vmware-converter-standalone-5.html"
rel="nofollow noreferrer">walkthroughs and howtos on the net.

The converter tool will make it easy for you to
copy the data off the old machine into the virtualized environment, the RAID volume
content can be copied as any other volume's content. Typically, you are getting the
choice to resize your partitions and filesystems as part of the conversion
process.