It's not the $500+ item I'm worried about, it's the $60 pain medication that a screener will pocket because "it looked suspicious". I can replace the $500+ item easily but I have to get my doctor to issue a new prescription for the medication.

Pretty much the same here. I put my backpack that has most of my nonvaluable junk in it (refreshments, books, spare toiletriest) first. Next, I place my laptop case followed by a bin with my laptop. Finally, I'll put my coat (in which I put my wallet, minus my ID which I have in my pocket, cellphone, sunglasses etc) and shoes (if necessary at that airport) in a bin. I try to make sure the last bin is ready to go into the xray machine (on the belt at the very least) and then I walk through the metal detector.

I figure that the first two bags give me time to go through the metal detector and my more valuable goods are in the machine, so they'll have less of a chance of getting stolen. As for the first two bags, there isn't much to steal there anyway, and who would steal a backpack over a laptop.

To the TSA screener's credit, when I got selected for secodary screening in May, inthe PHL US Express terminal, the screener made sure that my belongings were visible to me during the entire inspection. In fact, after wanding me and patting me down, he made sure that I was close enough to my bags while he inspected them to ensure that nothing was broken or stolen during the inspection.

Tru dat.

Another Precaution with your Laptop
 

So many laptops look alike, so I have placed a business card on the bottom and top of the laptop with clear packing tape. Most people won't know there is an ID on the bottom as well. I have been seperated from my laptop as well. Also, I have had the person directly in front and in back of me with the same laptop; it would be too easy to get them mixed up without an ID on it.