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At least with Windows 7, after jumping through a few hoops Windows Update will eventually work. However with Vista jumping through those same hoops doesn't work. I've tried just letting the Windows Update session do it's thing but after over 15 hours of letting it run it stays stuck on "Checking for Updates......."

I have that problem times 2.
I question your statement above. One of my PCs is a Lenovo laptop which got updated by stealth (I left it in sleep mode overnight.)

Turns out that this Windows 7 model from Lenovo is incompatible with Windows 10; Period. I don't have further info, perhaps a BIOS update?I was able to revert it to Windows 7, but haven't been able to restore software previously on it. Windows kindly removed it permanently.

The other is more problematic. It is my newest PC, a Lenovo i5 desktop, Win8/8.1/10 attempt. This was a deliberate attempt on my part willingly to upgrade to Win10. Before I realized that all my (relatively recent) and expensive purchased software is incompatible with Windows 10) Originally a Windows 7 Pro machine.

I am waiting for a class action suit to join.

This Acer Laptop came with Vista. I'm sure W7 could be loaded but I would only do so if the laptop was mine and if I upgraded the memory. It only has 2GBs of memory and as such will barely run Vista let alone W7 or 10.

Also, this laptop doesn't belong to me. It belongs to a female coworker who is not tech savvy and doesn't want anything but the original software on it. Hence my drive to keep it at Vista. Thankfully Windows Update started working this morning so hopefully I'll be able to get it done today.