I found the whole experience very simple to be honest. The reason for the upgrade is that I'm going to be installing a quad tuner HD satellite card into the server and thought I may as well do it on WHS 2011.
I had approx 1.7TB of data with about 2TB free. Disk config was 500GB system drive, 1TB drive, and 2 x 2TB drives. I decided to get a further 2TB so I could have some redundancy in the migration.
I added the new 2TB drive as a server backup drive and copied all my data onto it.
I then removed another existing 2TB drive from the drive pool and copied the data to that as well. This mean't I had 2 drives out of the pool with all my data on it.
Finally I removed my now empty 1TB and 2TB drives from the pool so all I had left was my 500GB disk with WHS v1 and old PC backups on it. This has been stored incase I need to use it again.
Next up I used the 1TB drive as my new system drive and installed WHS 2011
I then connected up my 3 x 2TB drives (2 full with data and one empty).
Using the inbult shares in WHS I changed the location of videos to one of my drives with data on and then moved the contents of my videos folder that I backed up into the new share. I then configured a twice daily backup of videos to the blank 2TB to give me duplication.
I then configured the remaining WHS shares to the other data drive and moved the data into their appropriate shares, again configuring where appropriate the twice daily backup.
I do miss DE and am making do without it. I can see me having some fun and games managing backups which I didn't have to worry about before. I am still concerned about the thrid party DE replacements with regards to data integrity and performance so will look again at them in a few months time.
Here are a couple of pics of my HD and share setup.
C/D drives are the 1TB drive used for the installation
F is the 2TB drive I'm using for the videos share
G is the second 2TB drive I'm using for photos, music and other shares.