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One of them is a laptop, why ssh to the server isn't an option? Set up tmux on the server so it always connects to the same session, so you can just continue where you left last time. If you need desktop support, rdp in gnome works really well.
E.g if you connect with this command, and tmux is installed on the server, it will start a new session named "main". If a session with that name exists it will connect to that:
ssh -t pi@192.168.1.2 tmux new-session -A -s mainAdd something to .bashrc on the server to always do the same if you work on that phisically:
I do plan to primarily ssh into my box but I'd still like plain old physical access, particularly while I get things like tailscale, DNS, and a reverse proxy setup.
Id also like to make sure my work PC and home PC are completely segregated for legal reasons, but I plan to to ssh into it from a different laptop anyway.
Use WSL on the laptop for ssh, that's actually a VM. VM separation should work correctly, or we have a much bigger problem. Just reset WSL, everything should be wiped related to the ssh sessions. Work IT would maybe allow that.
Note that some issue devices have VT-x disabled and the bios locked down by Corp IT for one reason or another, so a VM may not actually be possible from the work issue device here.