Hi,
How about something like this - the server starts up, but something is wrong - presently it mostly says "check filepaths and mapsize" - proposition: make the server diagnose the exact problem (i.e. the filesize problem that was lately reported) and propose a solution.
Example:
Error: MapFileSize 196 Bytes too small - Would you like to fix this? [yes] [no]
:P
That would be probably the only case where an automatic fix could be applied ... but that problem is definitely not common. Usually it's just that users mix up ML and non-ML map sizes. The example you refer to was the only one where I ever encountered it.
Well than just the diagnose part - Check the filepaths and mapsize is fine for me but it could be a bit more specific by simply checking the filepath and mapsize and giving the proper feedback i.e.
Filepaths incorrect - files not found
Mapsize incorrect - Expected size - XXXX, Actual size- YYYY
Even this would help us noobs ( :D ) find out what's wrong ourselves without having to run here and spam the forum ;)