ITunes keeps losing my music over and over

Question

I bought a MacBook Air - the top model - a year ago. I got into iTunes - not knowing what I was stepping into. On the Preferences dialog - Advanced tab - there are 2 boxes: one says to "Keep iTunes Media Folder Organized" the other says "Copy files to iTunes Media Folder when adding to Library" - I checked BOTH of these boxes.
I added my music files, imported CDs and bought stuff. ALL of my music files have been copied into the iTunes media music folder which is then broken down into directories by author, then by album and then the song files have track numbers appended to the file names. Whatever. I have about 500 music files now.
The problem is that almost everytime I open iTunes I have anywhere from 20 to 200 music files with an exclaimation point beside them. I cannot play them because iTunes cannot locate them. I have to click Locate and navigate into the iTunes media folder, author folder, album folder and then click the mp3 file containing the song and it plays - it fixes that song. Doing that for 200 songs? Are you kidding me?
I noticed that if I close iTunes and open it back up again most of the time the exclamation points are gone but it still will not play the songs. If I click the song it does nothing - it doesnt even give me the box to locate the songs.
This is driving me crazy. Obviously iTunes is not a practical, usable product. But it's the only way to get music onto my iPhone. Or is it?
I've searched thru the Apple support and they're taking lessons from Microsoft - they say the cause is that you moved the initial files and now iTunes cannot find them - they're essentially trying to blame their bugs on us - the users. So Apple - what about all the music I bought from the iTunes store? Did YOU move the initial files? Yes the CDs I imported have "moved" everytime I put my car in gear. The files I imported from my files system are still right there where they have been all along. And no - none of this music is on a removable drive. It's on whatever flash memory you guys put inside this thing when you built it. I refer to it as my internal flash memory - which takes the place of the hard drive most computers have. Seriously, does Apple have answers for this? Not just trying to put the blame back on me.
Had I not told iTunes to keep the media organized then would it keep all the music in one directory? Would this problem go away? Importing all my music again would take an entire day. If i'm going to go thru the trouble of rebuilding my iTunes library I want to solve the problem for good. I do not have time to keep fixing this problem.
I would just go and get a real music player that actually works - but I want to put music on my iPhone - that's why I use iTunes. I guess i'm screwed.
I suspect this has something to do with the fact that a MacBook Air does not have a physical hard drive - it uses flash memory instead - and since flash doesn't retain storage for long they probably have background processes moving files around so they stay fresh - and somehow when I close the computer and it "sleeps" and then wakes up it has "lost" hundreds of my music files because they were moved and iTunes doesn't have the new location?
Does anyone have any ideas? Has anyone found a solution to this issue? Is Apple ever going to fix this problem? If so - how do I get the fix?

Answer 1

If you click one of the marked library entries and reassign the proper file, will it work again?
Then iTunes seems to have problems to access the folder where you placed the music. User rights, removable drive locations... There could be many reasons.
The best way would be perhaps to define the media folder where iTunes can definitely access it, then import all files again and perhaps tick the option to copy the music files instead of just linking them.