Also important to note that Microsoft themselves have given advice for a configuration similar to this (the only difference being the network drive representation). If Microsoft sees no issue with recommendations for this config (IIS running on virtualized Windows on a Mac), then I see no reason why Server Fault should. I use virtualization constantly for Linux server development with Docker containers, why would I not also use Windows virtualization?

@GregAskew I think you, or whomever disabled the question don't actually understand the setup. There's no actual "network drive". Both the VM AND the files are on the same physical drive. The VM doesn't "know" that of course, but that's the actual reality. And using a VM for doing development in a different development environment is standard practice, and I'm certainly not going to setup a different machine for this when it's literally being used to replicate a site in order to migrate it. That would be a terrible idea. This IS best practices for what I am trying to do.

@GregAskew Like none of this will ever see production, it's entirely so that I can analyze the codebase and database locally, write the migration and keep feature parity

@GregAskew It doesn't, though. It's a LOCAL environment for development. The "network drive" bit isn't actually a network drive, it's how the virtual machine represents my actual Mac's physical hard drive. This is a perfectly reasonable setup for local development and testing. The only reason it doesn't work is because the VM software represents the parent drive as a network drive rather than a physical drive. It doesn't "tick any boxes" - why would I use another machine for development, when I am literally just replicating the original site so it can be migrated to modern frameworks?