A pressure gauge is nice but not necessary. I don't use compressed air to dry my boilers, (some do), usually a syringe with tubing attached poked thru one of the bushings. Make sure the tubing doesn't fall inside. Tilt to collect the water at one end, then suck the water out. I also leave the safety valve and whistle off for a while to help in drying.
Yes, you rotate the engine in reverse to suck oil into the steam chest/cylinder to lube. Don't need a lot and use steam oil.
No such thing as stupid questions, better to ask than... Oh Crap! What have I done?!