Check for water in your diesel fuel, cleaned your fuel screen, check for free flow of diesel from the tank and changed your main fuel filters. I have had algae cause a problem very similar to what you are describing. It just was not getting enough fuel to start after sitting over the course of just one winter. When you do change your filters try dumping out the fuel from the fuel filters into a clean bucket and see if the fuel is discolored or smells different than fresh diesel.
Also sometimes if it is really cold I have had luck with cranking the diesel with the fuel in the off position for about 10 seconds. Then wait about 30 seconds, then apply the glow plugs for same duration as you would normally for the conditions, then give it a little bit of fuel, not too much and then crank it. You have effectively heated the engine a little and it can make a big difference in starting in the cold. Also if you give it too much fuel when trying to start it can make it much harder to start form a few tractors I have had. Keep us posted. Have you checked to see if all of your glow plugs are working?
What's the status and specification of the batteries you are using?
just going from memory here old magnet but i think the specs below are correct for the batteries i put in it about 2yrs ago. and it was checking somewhere around 24.8volts to the starter.
Battery Electrolyte Composition:Acid
Battery End Type:Top Post
Battery Purpose😖tarting Lighting Instrumentation
BCI Group Size:27
CA at 32 degrees F:1035
CCA at 0 degrees F:840
Freight Class:65
Polarity:Left Positive
Reserve Capacity:140
Terminal Type😄IN
Volts:12
Even though you have the trip fixed, are you sure the glow plugs are not burned out?
Those batteries should be adequate if they are in good condition. I'd note your voltage reading. Batteries in good shape should produce 2.2v per cell = 26.4v for the two 12v batteries.
Old Magnet maybe onto something here as the cranking speed when the motor is cold is critical as it generates the heat and faster it cranks the more heat
Even in my mild climate and our very mild winter motors can wind over at what appears normal speed but still not fire straight up and the problem is its just not making the speed to make the heat
So maybe it is as simple as Old Magnets suggestion
Paul
You have a wonderful day. Best wishes. Deas Plant.