Just a link to a startup on youtube I know you don't have an operating pony right now, but this will illustrate the startup however you actually turn it over.
About 2:40 after the pony is warmed up, he engages the pinion clutch and begins to turn the main engine. Notice that there is some slight smoke from the exhaust. This is not enough smoke for the engine to run, the throttle is still closed until about 3:00 and it starts almost immediately after he opens the throttle. On a cold day, the time he spent running the pony motor with the compression release IN so the main engine is making compression and heating up the cylinders would likely need to be longer. Warming the main engine with compression release lever in should be done with throttle closed so diesel fuel does not accumulate in the cylinders before the engine is warm enough to fire.
If you have direct electric start, you will most likely have to use ether starting fluid even if it is quite warm. Just make sure you are able to turn the engine quite fast and you are getting fuel into it (lots of white smoke) and then give it a good couple seconds spray into the air filter hood. The ether will go through the oil bath air cleaner just fine and the engine should at least make some black smoke if not take off on it's own.
I do not have any qualms about using starting fluid on these old CATs. CAT original equipment for electric start models included a starting aid that had ether bottles that you put in a compartment and punched to discharge into the intake manifold. You have a lot more conrol over a spray can than that. Of course this also means that you can spray too much, but most folks are cautious enough about using it if they're starting their own tractor that it is not a problem. If it won't pop on a healthy spray of starting fluid, something is wrong!
Another link by KansasCat the host of the "SPRING FLING" get together for the last several years. This is to show what you should be seeing inside the injection pump housing if you need to go in and unstick the rack/a stuck pump plunger.
Here is another starting video done by Sasquatch who posts here and over on ACME. He explains a bit about the whole pony start procedure. His D2 is a lot tighter engine, not even a breath of smoke out of the exhaust with the throttle closed (no engine oil being burned in the cylinders!)