re: 1st time boat owner.

The best practice is to grease bearings TWICE, every time you take out the boat:

Before you leave the house
After you get back to the house.

Put this into the "taking the boat out" routine. This should be a methodical process, that forms a habit, like making sure there are PFD's for every passenger, making sure the batteries are charged, making sure the motor will fire up and run, checking trolling motor, trailer lights, etc.

You should have a list of stuff that is done at the launch, before getting on the ramp...unstrap boat from trailer, load coolers, bait, install plug, etc.

Reverse this process after trailering the boat.