Okay, I figured it out. Here's how to fix it when installing the beta:

Problem 1 Fix: Getting Wox Beta to see its assemblies

The ZIP folder is blocked by Windows for security reasons when downloaded.
Right click on the ZIP folder (before extracting), click Properties. Then select "Unblock".
Hit "Apply".
Extract the folder.

This will fix the issue of being able to run Wox--after inspecting the logs after the error, it was clear that Wox could find its plugins but could not load the plugin assemblies because they were blocked.

Problem 2 fix: Getting Wox beta to start at system startup

Now to the second issue: having Wox actually start up with Windows. First, I unzipped it to C:\Program Files, but no matter what I did (including settings tweaks), Wox woudln't start with Windows. The fix is to make the unzipped folder live in a folder that doesn't require elevated permissions to write to. So:

Copy the folder to a non-System folder (i.e. a folder that does not require elevated permissions to write to). I put it in C:\Documents.
Run Wox and everything is happy.

This issue, as far as I can tell, is because Wox is designed in such a way that it writes data back to the folder where it is contained, and so this requires admin permission to do anything (including start Wox at system startup). Hence, it wouldn't start at startup even though the settings were correct.

I may have some pieces of this off, but wanted to post the fix I got to work here so others can find it.

Uh oh!

do not work with windows 10 #279

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