For me it's ski race timing Software. Need a USB dongle and timing computer(a proprietary device that logs timestamps, prints and translates pulses offa wire into start and finish events to the PC Software) via USB. There's a lot of moving parts to manage, things like power to the USB, sleep etc. Bricking a ski race where thousands of volunteer, kid and coach hours have been spent in preparation for it is a nightmare. Last season our windows machines were in a Windows update death spiral on race day. The timing operators had no clue how to overcome it.

USB passthrough is trivial, as is PCIe passthrough which would let you pass the entire USB controller.

Yeah this is the way. I'm tented to go this route on my Mac but the licensing module won't work on ARM chips: Short answer: it’s not crazy to run Split Second in a VM—but only if you control the variables. The two biggest risk areas you called out (the USB license dongle and the timer I/O) are real. Here’s the straight path that works reliably, plus what to avoid.

Your go/no-go decision tree

1) If your MacBook Pro is Apple Silicon (M1/M2/M3): Running Split Second in Parallels with Windows 11 ARM is a no-go because the Sentinel/HASP hardware key that Split Second uses is not supported on Windows ARM. Thales (the dongle vendor) is explicit: “Sentinel HASP keys … are not supported” on Windows ARM; LDK works via emulation but not the HASP/HASP-HL USB keys you plug in.

i 100% get what you mean, it's still funny to me that you indirectly use a Windows update death spiral as an argument against using Linux :D

I'm all for Linux, The difficulty of keeping it on the shelf for a year and then running it on race days when it's in full update mode on a crappy mountain Internet connection was a near disaster.

I really wish this 3D Gerber viewer worked: https://www.zofzpcb.com/

You can feed it the output from Kicad, and if you include the ipc netlist it’ll even generate models. Great for doing a check before manufacturing, especially if the viewer matches what you see in Kicad.

Unfortunately I’ve never gotten it to run in wine.