Jim:

11 degrees is beyond limit for chain stretch (8 is replament time), so get a new chain in there before you play with the injection timing, or you will have to do it again.

Late valve timing gives low power and lower effective compression, and combined with late injection timing will give poor combustion, resulting in sooty pre-chambers and unburned fuel deposits. So does running cold all the time! New chain and a nice drive will fix all that. Lots of soot and oil can make the rings stick, lowering compression in any cylinder where they are well stuck.

Rack pin spring trouble usually shows up hot, but if it is really bad, could affect cold running too. My bet is that #5 is just low enough on compression that it won't fire cold.

That said, a leaking pressure valve or pressure valve holder seal could produce exactly your symptoms -- especially true if you get normal amounts of fuel leaking off with the cap nut loose but no injection. My 300D, however, didn't smoke at all, so I suspect timing to be most of the problem.

Peter

__________________
1972 220D ?? miles
1988 300E 200,012
1987 300D Turbo killed 9/25/07, 275,000 miles
1985 Volvo 740 GLE Turobodiesel 218,000
1972 280 SE 4.5 165, 000 - It runs!