How hard would it be to transfer a Windows based server to Linux?

Hey everyone, I’m in the process of starting a roadmap for integrating a full home server instead of using my gaming PC. Right now I have about 15 docker containers, stable diffusion, cloudflared, plex, and a few virtual machines with VMWare. I’m looking at making Linux (Ubuntu?) my main operating system for my (non-headless technically because it’ll be on an hdmi switch) new server machine. I’m a bit worried about transferring data over between machines, let alone operating systems. I’m looking for the easiest and most efficient way to make this happen. Please don’t hesitate to tell me if it’s probably more work than I’m in for.. as I’m fairly new to self hosting. Thanks in advance!