How many compatibility issues is MacOS realistically expected to spur? Windows DX felt unusable to me without a Linux VM (and later WSL), but on MacOS most tooling just kinda seems to work the same.

It’s not the tooling for me, macOS is just bad as a server OS for many reasons. Weird collisions with desktop security features, aggressive power saving that you have to fight against, root not being allowed to do root stuff, no sane package management, no OOB management, ultra slow OS updates, and generally but most importantly: the UNIX underbelly of macOS has clearly not been a priority for a long time and is rotting with weird inconsistent and undocumented behaviour all over the place.

Provisioning, remote management, containers, virtualization, networking, graphics (and compute), storage, all very different on Mac. The real question is what you would expect to be the same.

For server usage? macOS is the least-supported OS in terms of filesystems, hardware and software. It uses multiple gigabytes of memory to load unnecessary user runtime dependencies, wastes hard drive space on statically-linked binaries, and regularly breaks package management on system upgrades.

At a certain point, even WSL becomes a more viable deployment platform.