Has anyone had a problem due to dry joints in the wiring?
I've had all sorts of small problems with my wiring, most of which have either been poor terminations or inadequate slack in the runs. (tight leads which pull wires or plugs out)
I'd be double checking all the connections to and from the DCDC charger, including fuses.
All is good on 240 and good voltage at the Anderson and pin 2 on the vehicle.
If everything works well when charging on 240 V, then this will rule out most of the equipment and wiring, however if you haven't already, it would be worth doing a couple full charge / discharge cycles with the 240 V to really check it all out. (e.g. Charge it, and then flatten with the fridge for a couple of days, charge it back up, and check battery SOC, run times, etc are as expected.)
Although you're getting good voltage on the vehicle anderson, there could still be an issue on the vehicle side. When there's no load (everything off) a dry joint or poor connection / termination can still show a good voltage, however this will quickly drop off under load. When checking the 12v from the car, check it in an open circuit condition (trailer disconnected), and then under running conditions (DCDC charger running), preferably at the DCDC charger itself. This will check from the alternator, through the dual battery isolator, vehicle wiring, Anderson plugs, and trailer wiring.
You will need to discharge the batteries a little bit so the DCDC charger will pull the full load, otherwise you can disconnect it and try plug a few 12v appliances in (the higher the load (within limits say ~30A) the better the test.)
If everything else looks good, then it's either the wiring from the DCDC charger to the battery (including fuses, etc), or it's the DCDC charger itself.