I guess I should come at it from the other side:

If you have 1 iscsi target box and it goes down, you're dead in the water.

If you have 2 iscsi target boxes that replicate and one dies, you are OK but 
you then have to have a 2:1 total storage to usable ratio (excluding expensive 
shared disks).

If you have 2 tiers where you have n cheap back-end iSCSI targets that have the 
physical disks in them and present them to 2 clustered virtual iSCSI target 
servers (assuming this can be done with disks over iSCSI) that are presenting 
the iSCSI targets to the VMware hosts, then any one server could go down but 
everything would keep running.  It would create a virtual clustered pair that 
is basically doing RAID over the network (iSCSI).  Since you already have the 
VMware hosts, the 2 virtual ones are "free".  None of the back-end servers 
would need redundant components because any one can fail, so you should be able 
to build them with inexpensive parts.  

This would also allow you to add/replace storage easily (I hope).  Perhaps 
you'd have to RAIDZ the backend disks together and then present them to the 
front-end which would RAIDZ all the back-ends together.  For example, if you 
had 5 backend boxes with 8 drives each you'd have a 10:7 ratio.  I'm sure the 
RAID combinations could be played with to get the balance of redundancy and 
capacity that you need.  I don't know what kind of performance hit you would 
take doing that over iSCSI but I thought it might work as long as you have 
gigabit speeds.  Or I could be completely off my rocker. :) Am I?
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