I am having extreme trouble portalling my map... I have watched all the video guides, and sure they tell me how to portal a perfectly square room with square windows or a perfectly right angular outside area, I am struggling greatly to get my map to portal successfully, I have got one area at the start working ok, but the rest,
How would I go about portalling an area like this? with a building in the way with its own windows?
And a staircase coming from underground.

Or an area with angled buildings and another underground entrance:


And testing my existing portals, they don't even work!
Adding a Caulk brush to see the effect like in the tutorials:

In game, note brushes still render behind the portal, even though the Caulk blocks view of it theoretically:

And note: the building with portals in the first picture, they do not show in game, so they are not working for some reason.

Errors galore:

If someone could point me in the right direction so I can finally portal my map correctly then it would be massively appreciated!