Most of the “software that runs only on Windows” runs perfectly on Linux with wine, including the installation software, and the integration into the app launcher on all of the Linux distribution that I know.

For a widow manager, I don’t use one, i have many virtual desktop and as it’s smoother than in Windows, I use only that (i don’t remember how virtual desktop works on ubuntu)

Première run really badly in VM, and run it with wine is highly messy, do to poorly designed Windows install soft and plenty of missing dependencies, there are linux alternatives that do nearly the same job : KDEnLive, Shotcut and Openshot.

That all I can tell for now, I hope it will help you a bit. Ps: try other linux distribution before doing an installation to find the desktop manager that you prefer.

*wake-on-LAN

Give a try to ZeroNet

Velorem and Endless Sky!