Do I have to reinstall XQuartz every time I upgrade MacOS? I use a slightly weird setup where I will connect from my Mac laptop to a linux machine, using ssh -X, and from there connect to a Windows machine using rdesktop. This works just fine, but whenever I update Mac OS (even minor upgrades), I find I have to re-install XQuartz. If I don't, rdesktop fails with the message ERROR: Failed to open display:. After I re-install XQuartz, it works as expected (no reboot or log out or anything, just opening a new connection with ssh -X).

Is there a way I can avoid having to reinstall XQuartz all the time? It gets a little annoying.
Not really - the tool is one that's very command line - run and bind against the specific OS that it's installed in.

I realize this may not be the answer you like, but I'm actually floored it keeps working as long as it has. Here's to hoping this is our main complaint on this tool.