Hi all, just updating this with the weekends progress. So I checked timing, this was all spot on. Cam slot, timing chain links and the slot in the fly wheel all lined up. Next I reset the bump clearances on the injectors. Still smokey but it might be a bit better.
While I was underneath to check the flywheel timing slot, I noticed that the fuel pressure regulator was indeed leaking so this could indeed be the cause of the need for priming as Tins suggested. Has anyone had success with just replacing the pressure regulator part rather than the whole assembly? Like this one Land Rover Discovery TD5 Fuel Pressure Regulator Repair Kit BOSCH+W/Shop Manual | eBay
I had another thought, would crap old fuel give me a smoke problem? The fuel has been in there for quite a few years now. I might drain that and refill next step.

