I've had a number of T-stak units since early summer - 3 deep, 2 flat top, 5 two drawer, and a long handle. They're used around the garage and house for DIY work to store drywall, electrical, and plumbing tool kits along with several for misc. supplies. 3 of the two drawer are empty for possible future use (got decent deals and decided to buy extras to get to free shipping on a couple of different orders).
If you're going the T-Stak route, take a look at the Trolley instead of the cart. It's more expensive but the tall handle and larger wheels of the trolley will let you go places the cart can't since it hangs up on the smallest of obstacles on a concrete floor.
Dewalt T-Stak Trolley
I bought a cart and changed my storage layout almost immediately when I got free metal shelving so it isn't being used right now.
I don't have any of the deep drawer units but several of the 2 drawer units as I said. They're alright but if you're planning to load them down heavily or stack them high I could see the drawers sticking when you open and close them.
Overall quality of the T-Staks is good for the price they charge - especially when compared to Festool or Bosch systems.
Everything in your pics should fit pretty well but the socket set in the blue case may be a little tight. Let me know if you want any interior dimensions.
