If there is a store near that has Macs on display, go check them out and try your most used workflows as best as you can. Even a used M1 Mac will run the newest macOS so that should be a good initial impression.
Day to day tasks are no problem for any modern OS. Internet, Mail and the like. Look for the not so daily tasks to get a feel of the system and if it can do it a way you can arrange to.
Interoperability between devices is best within the ecosystem, but applications like local send work cross platform and can replace something like Airdrop between Apple devices pretty well. If you have your documents and data on a self hosted system or something like Dropbox as well.
I personally use both on my notebooks, and I always liked the Macs for pretty much just working. When having to troubleshoot and support windows machines at work all day, that is a big plus.
This. Tailscale just works and has functioning VPN on demand for your networks.