First thing is is the belt on the exciter generator mounted on top good/tight?
An unknown generator like that can have major shorts, burned windings etc, so it might be a good idea to have it checked with a megger (after disconnecting any connections to the regulator-regulators don't like the high voltages applied by a megger). If you don't have one and it looks pretty good, you can let it test itself when it makes electricity. If it burns up, it will definitely have to go to the shop ;>)
Then check the brushes and sliprings in the main alternator, sliprings should be clean and brushes have tension on them, not be cocked in the guides because they're too short etc. The exciter generator on top has a commutator and brushes too. There are commutator/slipring dressing stones you can buy to clean these. They are a soft stone like limestone which wears away quickly as you hold it against the spinning ring. I have also used sandpaper in a pinch.
Maybe dry Bonami powder on a rag?
Once you get through with that, if it still won't generate, try to identify which brushlead is + (usually F1?) and which is - (F2?). Rig up a battery to flash the field with. You want to run the set and touch the BAT+ to F+ and BAT- to F- and see if AC voltage will build up. If it comes up, it should build up to full voltage quickly so remove the flashing jumpers as soon as the voltage begins to come up. If it comes up, but won't reach full voltage and hold, you will be safe leaving the flashing connection on until you see what final voltage you will get. You should get some fraction of full output voltage depending on the voltage you apply to the field.
Flashing restores some magnetic field to the iron. The generator has to have some "residual" magnetic strength left from the last run to begin to make voltage. In the case of your set with an exciter on top, the exciter is the component that has to make the starting voltage, but I believe flashing the brushes on the main generator will also flash the exciter at the same time.
Your generator probably also has a flashing relay that automatically connects battery voltage to the exciter field until it builds up voltage. If this functions properly and your set has batteries (does it have any?) it should take off on it's own every time no matter how long it has been since the last run.
D2-5J's, D6-9U's, D318 and D333 power units, 12E-99E grader, 922B & 944A wheel loaders, D330C generator set, DW20 water tanker and a bunch of Jersey cows to take care of in my spare time:D