So this is where I'm at now, I've managed to solve the original problem by using compression fittings alone and re sizing some of the copper.
NOW I've got to deal with the inside.
I've just done a test run off with some water, and the run off stops at the point where the hole is, not where my hop filter reaches down to (see picture)
I managed to get it to work by filling the tubing for the run off with water, and using the water falling out to pull the rest of the water in the pot through (if you get what I mean).
Will this system only work if I come up with some sort of syphoning device or get a pump? Or is there an easy work around that I'm missing?