There's nothing silly about those reasons.

I call it silly because essentially I’m complaining that I don’t like setting up a service on an OS I don’t normally set up services for. My quibbles with that process can in part be addressed by crafting a terminal based workflow to configure the host and enable the service on my desktop, skipping the GUI completely. E.g. I’m sure I can do Task Scheduler shenanigans through powershell. More experience would help sand down the rough parts I experienced.

Now the product decisions behind the OS giving me the icks… The terminal can’t (completely) help with that ^_^

Eh those applications can both be run in linux without issue.

They are likely to have more issues related to getting the drawing tablet configured correctly.

The rest is just having to start from scratch and lose the decades of windows experience and intuition which can make things painful as that type of thing cant be replaced without time.