Cuttler Bearing

hello help!
So my bottom was getting its monthly cleaning and the diver either grabbed the prop or the shaft and wiggled it back and forth. I could feel the thud, thud, thud.
He said my “bearing” was shot only on the starboard side. Im believing I should just change them both.
I just purchased the boat in December so Im not sure what was maintained or not.
So, my questions are this.
Since I will be pulling her out to be fixed, does anyone have a general idea on what Im looking at to have both repaired? Also, cleaning the bottom thoroughly. I might even repaint. Also all zincs I will be replacing to.
Im pretty machanically well to do. I like fixing things on my own. Should I buy the shaft tool kit and just replace them myself, and change the zincs and do the bottom clean and paint all in one pop? Im curious to if I will be saving myself a couple thousand or only several hundred.
The liveaboard boat lifestyle and vessels over 21 foot, mine is a 345 Sedan Bridge, is just whole new can of worms to me. Expenses and mobility of the boat is just a completely different ball game. Not like I can just back the trailer up, pull her out of the water, fix it on the fly and drop her back in the drink.
Since I am living on her I will need to make a completely different arrangement on time and material needed to do said projects.
So if any of you experienced captains can give me any pointers and suggestions, please do. Im all ears.
Im 51 years young and see my remainder years living on her for the rest. If anything, I would be selling her to step up to a larger woman but I want to treat, fix, repair, maintain her like she’s my last purchase.

Thank you in advance.
Ps. Is it cutler bearing or cutless or? Thnks!
Capt . Wardy

First Wardy, it's a Cutlass Bearing not a Cuttler Bearing.

In my opinion, if you have to pull it out of the water I would do everything below the waterline I can while she's out. Replace the cutlass bearings (2), take the props to a shop and have the scanned and trued, check for blister and repair if needed, paint the bottom, check trim tabs for proper operation and replace all zincs. The cost will depend on how much you can or are willing to do. I've been working on my own boats for 50 years and there are still some things I prefer to pay the experts to do. And you may need to check around....not all boat yards allow owners to work on their own boats.
Good luck
Shawn

What ^^ he ^^ said. Also a good time to change out any transducers that don't meet your particular needs and maybe install under-water lights if that's your thing.

Don't forget to paint little fish on the bottom to make the lunkers think you are a school of bait fish

The tool cost around $350 and you'll use it once. Do a search and maybe you can rent it from someone. I was going to be charged 1-1/2 hrs per side. I ended up doing it myself. Not too bad if you have some know how.

Nothing to do with changing the bearings but keep the old ones and polish them up. They make a great thing to put on your desk at work or a place at home where guests will see them. They just look neat and make a good conversation piece.