Hi itronin - Thanks for the feedback. I think I'll have to see how it goes once January 1st hits. I think you are right about needing to re "order" the products, just to get the keys again.@BennyT, I *just* went through this. It is a bit confusing.
edit: Oh - one thing I'll note. I pay year to year so maybe that makes a difference for the process I used?
I renewed my membership before it expired and I waited and waited and my keys never showed up. there's actually some bit of a grace period after the original VMUG order date before they will expire out as you are seeing in your vsphere client: 30 days.
I believe their description of the process is poor.
From what I figured out - reading posts etc you have to "reorder" your VMUG products each year (that is explicitly said somewhere in the VMUG process). The update keys automatically appearing - I dunno but the reorder generates the keys and then they do appear and you simply load the new keys in your installation reassign and all is well. They keys showed up within an hour of my reorder order (IIRC).
Maybe I'm doing it wrong? but it worked for me.
I just have to wait until after my expiry date is reached (for me that is Jan 1st 2020) before I can reorder the yearly license keys