To help you with the terms, what you're looking at from above is the top plate. Frequently there are two 2x4's for a top plate. Two boards are used for added structure at the joints and extra fire proofing. This gives you about 3" of wood to drill through.
As ChrisF mentions, you should run a stud finder up and down the wall cavity near the halfway point to see if any fire blocking has been installed. This would be a single 2x4, and will almost always be in a wall if the ceilings are over 8' tall.
You'll significantly reduce the odds of insulation in the wall if you are doing this project on interior walls. You should also be avoiding any electrical in the same wall cavity (between the same two studs). You would see an outlet, switch, or wire coming out of the top plate if this were the case.
As for the actual wiring, I've used these low voltage mounting brackets for the hole in the wall. Place the bracket on the wall where you want the opening, mark the corners and sides, and cut out the drywall with a drywall saw. Test fit the bracket and file back any spots that are blocking you until you get a snug fit. Then bend the tabs back into the wall and tighten them with a pair of pliers. On that bracket, I use a modular plate (these comes with more openings if you need them) and then an ethernet jack mounted in the plate. You can also get jacks for cable, phone, stereo, etc.
Couple problems I see. First is the textured ceiling. You'll never be able to open that up and patch it without being obvious, the texture is something that just isn't done these days. Second, the exterior wall should have insulation in it, so you'll end up fishing the line through insulation and the vapor barrier.
Instead, I'd suggest running the line around the floor if you can get it to a convenient wall anywhere in that room. Use some fasteners to keep the cable at the base of the wall to run it around the room:
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May I introduce you to smurf tube? It's actually designed for the job, and meets your flexibility requirement.
(Technically ENT (Electrical Nonmetallic Tubing), and it comes in non-smurfy orange as well as smurf blue.)