1) Until now, we have recommended to our customers to choose one of the web front-end servers and make changes to the editor configuration files there. After that, you should schedule a task to propagate those changes to the other servers. You can use the windows task scheduler and create a small batch job using xcopy. The xcopy command has a /D option that will copy files only if they are newer than the ones at the destination.
2) if you want to make some default changes to the configuration files, you can just repack the solution (.wsp file) and add them there. This way the changes will be applied immediately after you join a new server and deploy the solution there. The .wsp file is actually a normal windows cabinet file (.cab) so you can extract it with most archiving software (or windows cabinet viewer). You can also use the makecab utility to create a new .cab file later with the changes.
the Telerik team