That is a great idea !..A constant pressure source above the IP.....I will do that next time I do the IP...
I could kick myself for not thinking of that........
I know about the hand pump not being a good constant source of pressure...
That is why it is so hard for new folks to figure it out....It drives some people crazy trying to pump and turn the crankshaft and count the drips and position the pump all at once and like you said temperature,fuel viscosity,hand pump pressure and other variables overwhelm some new timing attempts.....
The FSM has a (high pressure method) that gets around the constant pressure problem but who can afford the set up...
I think your bucket method is the next best thing.....It would be nice to have a write up with pics in the DIY section....It could be the (leathermang constant pressure drip test)....Good info..!

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1978 Yellow 300D (The Mustard Toad)
1980 Blue 240D (The Iron Toad)
1989 Grey Mitsu.4WD Mighty Max Pickup (Needs a Diesel transplant bad)

(Open the pod bay doors HAL)

Tried the drip tube method today. Did everything per FSM along with another experienced forum member, so I am fairly sure everything was done right.

The problem is, I couldnt get fuel to just drip on its own like I think it is supposed to. Fuel would drip out swhen I pumped the primer, but would not hold pressure and drip afterwards. For what its worth, the timing was about right if I went by the drips that came out when i pumped the primer.

I have the updated primer pump.

Any ideas as to what this may mean or where I may be going wrong?

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'85 300D, 'Lance',250k, ... winter beater (100k on franken-Frybrid 3 Valve Kit)
'82 300D, 'Tex', 228k body / 170k engine ... summer car
'83 300TD Cali Wagon 210k, wife's car

Look back at post #15 on this thread and read leathermang's method for this....It is a great idea of his that I will use next time.....It explains about the pressures.....and the best way to get this right...

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1978 Yellow 300D (The Mustard Toad)
1980 Blue 240D (The Iron Toad)
1989 Grey Mitsu.4WD Mighty Max Pickup (Needs a Diesel transplant bad)

(Open the pod bay doors HAL)

A full fuel tank worked for me. '82 300D.

I was just thinking that to start this proccedure with a fresh fuel filter might be a good ideal. If the existing filter has not been changed out since the ice age it might pose a slight restriction. I wonder if enough to skew the test a little? I do not really know much about this other than the original proccedure certainly was based on a free flowing filter.
This in no way changes the advisability of the gravity can wisdom as a member mentioned. It makes good sense.
A constant pressure will need to be applied on a contained volume of diesel fuel to drip. If there is no air in there to build up a reserve pressure source. Although to save argument some pumps might have an air bubble in the injection pump or fuel filter to compress and provide a contiuing pressure source. Other than that when you stop hand pumping there is no residual pressure available if there is no air. A basic hydrostatic fluid law? The drip is going to stop. Unless there is some fuel in fact higher than the bottom of the loop of the drip tester as well is the only exception I can think of. Clear as mud? Or just muddled thinking?
I also suspect to have a constant the applied pressure or elevation of the can should produce a constant fuel pressure of just under the return relief valves release pressure. Around six pounds? For general purposes it is probably overkill to some extent. Although I think the manufacture thought it might increase accuracy. I suspected this when someone mentioned there is a mention of a specific factory kit to pressure up for the test. The test pressure cannot exceed the relief valves pressure relief point so it would not be higher. There would be no point in that I believe,. I just knew I should have gone to bed while I was ahead and before reading anything on pump timing.