Concerning updating, all you basically need to do is overwrite some of your existing files with new files from the updated archive. These files are Aonio.exe, Aonio.pdb, and in case of your major update also LiveForSpeed.InSim.Aegio.dll and LiveForSpeed.InSim.Aegio.pdb.
Problem is the configuration file. You may use your old config file, but some new options will be sort of hidden to you, using Aonio defaults instead of what you'd like to use.
My suggestion: 1) Rename your old config file. 2) Copy new config file from updated archive. 3) Open both files, moving items one by one from your old config file to the new one. 4) At the same time configure all new options.
There's not so many lines to move (maybe 20 or 30), it will take just a few minutes. I would certainly suggest to update, because all new features in updates are optional.
I have just uploaded a slightly modified version 1.4.4 that would reinitialize when you type !aonio re or simply !are.
If you are on a server without Airio or Lapper, making your Aonio commands visible, you can always start the command by /o, for example /o !are. It will be hidden, but still executed.