Organizing itunes help, please

hey,
so i'm re-loading itunes off an external hard drive after having had to erase my laptop's hard drive. in the past i've had some problems with itunes that i'm hoping to avoid this time around:
1/ if i changed a track name on itunes, the file name on my hard drive would remain unchanged. this is a problem in case i have to re-load itunes again in the future--i'll be stuck having to completely reorganize my entire library/re-name every track. is there a way to avoid this (ie. make sure that any changes i make on itunes are made on the music file as well)? or would you suggest i change track information on my external hard drive before loading to itunes?
2/ when i delete a file off my itunes library and select to move the file to trash (instead of keeping the original file on my hard drive), sometime the file isn't actually erased...so now, for example, i'm re-loading itunes off my external and i'm seeing tracks that i had "erased permanently" long ago...any thoughts as to why that might be happening?
thank you!
Mac OS X (10.4.10)

or would you suggest i change track information on my external hard drive before loading to itunes?
Most iTunes users just manage their music in iTunes and avoid touching the files. But to answer your question, let's put it this way: if you are going to rename the file, do so before it is added to the library; once it is in the library do not rename or move it, on pain of receiving the dreaded exclamation point.
i'm seeing tracks that i had "erased permanently" long ago...any thoughts as to why that might be happening?
Here is one scenario by which that could happen: you have preferences set to "Copy files to iTunes music folder when adding to library." You added, it copied, and the original file was left in place. When you deleted the library entry, the copy in iTunes folder went away but the original copy stayed on your drive even though it is no longer in the library.
Windows XP & 30GB iPod

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