Since I am way out of the loop on IT/Server OS things and tired of reading all the marketing crap on Microsofts website, can someone just please tell me if I should upgrade our current Windows Server 2008 Standard edition to R2 when it becomes available. I can't figure out all the licensing either, is this considered a PAID upgrade?
Yes, R2 is considered a paid upgrade, its effectively a new product.
The main new features of R2 that may be of interest are:
So whether or not you should upgrade really depends on whether these features will be of benefit to you, and the cost justifies the upgrade. If they do, go for it, if you have no need for them then stick with what you have if its working well.
Whether you should upgrade or not will depend on whether you need any of the new features. This is pretty much the answer to any "should I upgrade my X to version Y?" type question... nobody can answer that except you as it very much depends on your needs.
As for licensing, R2 editions of Windows Server are separate SKUs, i.e. a different product with its own license. So yes, it is a paid upgrade.