I have an important update on this. I think it's mostly good news.
I debugged the issue via a virtual session with the person that develops the WildFly plugin for NetBeans. What we found out is that the management port I was using, 9999, conflicts with Netty. For context, I had to specify a port override since 9990 commonly conflicts with NVIDIA drivers on Windows. As soon as I used a port other than 9999 and 9990 everything worked absolutely perfectly. As soon as I switch to 9999 everything basically breaks without a real error message indicating the underlying issue. Using 9990 on the other hand clearly indicated a port conflict.
I tried the same thing on Eclipse with exactly the same results.