By default preloading just caches mountpoints in the default VFS file and thus this could mean just a single directory if you only have a root entry. It is up to you to specify what else it should preload. In practice if you have large directories/fanouts that take minutes to load the first time that aren't mountpoints then specify them manually in the .ini file so the server can do the work ahead of time. This is especially true for large fanout dirs on networked drives.
The Delay= setting which determines whether the server should wait around and finish caching the dirs before allowing connections to the server fundamentally changes the way preloading occurs. With Delay=False the server queues a low priority task onto the internal worker thread queue and it will process the directories one by one. If Delay=True the server hasn't really started yet, and thus there are no worker threads, so it spawns a new thread per mountpoint / manual entry and does the preloading in parallel so completion time is basically the slowest task to finish. Remember though that ioGUI/etc won't be able to connect while this is going on because that's the point of this setting...
If you are experiencing crashes at startup try switching the Delay= setting and see if that makes a difference because the =True option is the one I used for testing most of the time since it seemed far more fragile with all the thread creation/synchronization/etc.
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