Mike,
with that packing list you can exactly follow my method. Put the socks in the shoes. That's where they end up anyway. Put both shoes in the bottom, though. You'll see, better for weight distribution. It prevents the roller from tipping over too easily.
You almost don't need the suiter in your case, because you don't carry a jacket but would wear it. What you can do is to use the suiter compartment instead of the shirt folder. That should work quite well. Just don't put your pants in there, too.
Since you don't have a real core without the shirt folder you could get a packing cube for the t-shirts and underwear. Use that instead of the shirt folder as a core to wrap the pants around. Make sure that the packing cube actually is small enough so that it compresses the contents. You want that thing to save some space at least. Most people use cubes and don't use them as compression devices. This is a bit stupid (sorry) because it adds bulk and weight.
For my in-flight bag I use an Eagle Creek pocket. It has a carabiner and is made of transparent plastic with mesh around it. It's about the same size as a 311 bag. Since there will likely not be any liquids in there, you don't have to take it out of the main bag. So use whatever little bag you deem appropriate.
For the valuables I use either a ziploc or put them in the in-flight bag. What I do even more often though, is to put the valuable in jacket pockets which either have a zipper or at least a button to close them. The jacket needs to go through the x-ray anyway, so there is no additional step.
You say the toiletry bag is a problem. Like you, I have identified those big-... heavy toiletry kits as a problem to light packing. They weigh almost one pound when EMPTY. So now I use ziplocs for my razor, hairbrush, nail scissors and the other non-liquids I have. It works great. If you need more than one, you can split your stuff up e.g. razor and hair brush in one baggie, then toothbrush and scissors in another bag. You just saved yourself 1lb and tons of space. You'll see. Also you want to go with as small bottles of toiletries as you can, and avoid glass bottles of cologne.
Risk of theft is always there. See my thread on theft prevention in the travel buzz section.
The thing is that if you pack the way I told you, you will pack lighter and more organized which will allow you to carry on and not worry about theft.
Till