After further research and doing a firmware rollback I have come up with some conclusions:
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The current firmware does not support this feature. I believe it actually may have been removed, which is disappointing. I think it is a valuabe feature and would encourage people to buy multiple WDTV SMP devices if it worked.
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Upon rolling back to 1.16.13 I was able to get resume play across devices through the Media Library method. However it only worked with one device was plugged in at a time.
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The moment that 2 devices are plugged in and connected to the network, I would no longer be able to resume play on mutiple devices. My guess is that the Library would become corrupt in some way. I am not sure how to troubleshoot exactly why this is happening.
My guess is that the .wdtv folder/files that are created through the Media Library Compilation process cannot function properly with 2 SMPs. I guess it could be possible for a hub to handle that information differently.
If anyone else has thoughts about who to get 2x SMPs to resume play through a common Network Share on a Windows7 machine, let me know. Thanks