Either of those two engine oils will be appropriate for year round use, but in extreme cold, you probably should use a 5W or 0W synthetic.
The inside back cover of the parts book has the capacities for all the various oils on the machine. Transmission should be filled with a transmission oil meeting the current spec of CAT TO-4. On the other hand the cheaper universal “ tractor” fluids meeting the older TO-2 are probably better than the 10W motor oils originally specified. You can use the TO fluids in the hydraulic tank, the cheaper universal transmission fluid or a hydraulic oil.
I noticed the operators manual recommends 10W or 30 W motor oil in the final drives and differentials. I think this is a mistake and you will have more reliable machine if it’s worked hard by using a gear lube in those compartments. Again, in extreme cold a 50W synthetic would be appropriate but a standard fill for year round use would be 75-85W gear lube.
Brakes on the early ones like yours are air assisted hydraulic and are not noted for being very effective. Later machines are strictly air operated and have no manual braking available if the air supply fails but are generally preferred to the air boosted version just for the simplicity and effectiveness. With any of them, keeping brakes adjusted up is very important. Mine had enough oil leaks that i had oil soaked brakes on all 4 wheels so I had to replace all the seals before I could get much braking effort out of it. Your brake booster cylinder has a fill/check plug on the end of it and should be kept full of clean oil. Should be some pictures of it in the service manual. The master cylinder itself uses a standard DOT brake fluid, NOT an oil. It’s under the floor plates. If you need to bleed the brakes the book suggests using a pressure bleeder but it can be done by pumping the pedal. There are two bleed screws on the booster itself and then one at each wheel.
Look in an operators manual for a fold out maintenance guide. The capacities and fluid types of the various compartments etc are also listed on that. But if you strike out on both those, the engine is listed at 14 quarts capacity. I would count on needing close to 4 gallons when changing the filter. Note the oil level is checked with the engine running at idle. Best to check is after engine is up to operating temperature.
The valve cover gasket is nothing exotic, as I remember it’s a standard cork gasket and yours is probably gotten hard and possibly cracked at the hold down bolts if someone over tightened them attempting to stop it seeping. If nothing else you could remove the cover and clean the gasket up so some silicone gasket maker would stick to it. I’m sure you could get a new one from your CAT dealer. While you’re in there I would take the time to adjust the valve clearances as that is a service that is frequently overlooked
You really need this book. I did a search on eBay and all I could find for your machine is a reprint. Note the 922 was made for a long time and there are several different engines and differences in the brakes etc, so you need the manual for 59a1-up so it will be applicable to your machine.
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