I'm getting ready to do my annual maintenance (3 years too late

1. is it a big job to do it?
2. do I have to pull the propeller shaft to do it?
3. if I pull the shaft, should I change the bearings? (I'm assuming the horrible chatter I hear when going up and down swells is a bad bearing... IDK)
4. is it worth doing if all I am dealing with is a little dripping in my bilge and a little grinding noise on the occasional big wake or high seas (lake erie) ?
Thank you all for the input - good and bad lol. If any of you are at Brand's Marina in Port Clinton, stop by and say hi. You can't miss the boat

D