The only potential problem I can see is wind. I would alternate the pickets on each side of the rail. This allows the wind to pass thru the fence. This design does allow for viewing thru the fence if you are close though. Cars or pedestrians passing by would have a difficult time seeing thru it. I would drill a hole on three sides of your socket. Weld a nut over the hole. This will give you a setup similar to a Christmas tree stand. By inserting bolts in the nuts it will allow you to adjust the post to plumb it.
The chain link fence folks have all kinds of fence post caps that could be used to keep the rain out. Also there are nylon caps for EMT. You could convert the tubing to iron pipe threads and install threaded PVC caps. As to the holes and lacing the cable, before installing poles, I would put them on the drill press and pre-drill.
Best Answer
You might use a "barrel strainer" to tighten each horizontal run of wire.
Otherwise you can buy tensioners and "through-collar" kits specifically for cable fencing systems.