I've never bought anything but gift certificates directly from the iTunes store for other people for this precise reason- they have way too much control over what YOU have LEGALLY purchased from them.
Allowing customers to purchase ANYTHING online comes with a risk- one that should not be borne by the consumer alone. Apple's irresponsible and reckless purchase policies that are fueled mostly by a greed and an unhealthy desire for corporate expansion have led to this unfortunate situation, and now it's time for them to except at least partial responsibility and let the insurance companies take care of the rest.
As for your situation, here is my recommendation to you:
-Don't try to contact Steve Jobs, because you'll probably just get a long and useless reply back from a member of his legal team telling you that you are just going to have to take it hard without a reach around on this one.
-Stop purchasing things from iTunes. The amount of time that you spend jumping through their flaming DRM hoops like a trained circus animal could be better spent on a new hobby, or some other constructive activity like volunteering at a soup kitchen or reading books to school children. In my experience, things that you "buy" from iTunes can disappear if you format, or lose or damage your machine, or too much time passes, and getting them back is not as easy as Apple would have you believe.
-$5000 you say? It's very noble that you've contributed so much to all of the artists that make the music and films that inspire you and improve the quality of your life; however, the reality of the situation is that most of the money you have spent has gone to the bloated paychecks of the fat cats at the production companies, most of which they spend on expensive foreign cars, and cocaine to snort off of the backsides of prostitutes. These individuals are the reason that music and film has become less and less about artistic expression and more and more about creating the perfect formula for selling the maximum amount of homogeneous refuse. If you can say "Hollywood" without gagging and choking back vomit, then you obviously haven't watched enough Hannah Montana, listened to enough 50 cent, or seen enough candid photos of Brittany Spears' vagina.
In short, stop supporting them. Get your music and film library back, but don't spend a dime.

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ROW! ROW! FIGHT THE POWAH!!