RE: Greasing propeller shaft
The yellow cap on that bearing indicates it has been supplied with a Sealmaster proprietary grease. Any good EP grease will work.
Without knowing the type of seals used on that bearing, the best advice is to gently grease it until you see some old grease extruding from the seal.
Sealmaster sells an automatic greasing system that produces 70 psi so let that be your guide ... don't apply 1000 psi very rapidly by greasing it like you did your car or you will blow out a seal and those roller bearings will fail in short order.