I see X thousand dollars in your post
If you were to buy Windows Server 2008 R2 for less than $1,000 and then $75.00 per CAL, I hardly think you would spend $10,000. We don't know though, because you haven' specified how many users you have.
MultiPoint Server is a great solution if you already own SBS 2011 Essentials and has 1 + 1 licensing. You still need user CALS.
I don't know why you say, "Upgrade to Server 2008 R2." I wouldn't consider purchasing 2008 an upgrade. It would be completely separate if used as a TS. And, I don't understand how it would take a load of work. You just set it up as a Terminal Server.
