Looking for suggestion/comments/ideas

Boating is a great way to loose money.

I was in the same situation. My 150 Mercury died and i decided to put a $13,500 new one on a hull worth $1500 on a good day. I liked the hull and knew the hull. I’m sure my transom has some water in it and the stringers too. The great thing about outboards is the ease of taking them off. Four or six bolts, undo some cables and it’s done.

I figured if the hull gave out, i could sell the newer motor and only be out $7000 or $8,000. That was 10 years ago.

Best decision I’ve made in a while. New engine gave me a lot more confidence than the 20 year old did.

I did replace the fuel tank when i repowered.

I say, if ur transom is decent and u like the boat, repower.
 
In 2004 we did a complete refit, repower and repaint. No transom work or stringer work necessary. Invested way more than I knew we would ever recoup, but the wife and I figured she'd be our last boat as in forever (we were in our early 40s then). All good until 2016 when I made the mistake of leaving her in the water when Hurricane Mathew came and put her partway under at the dock. She got a little battered and beat up and the engine went under. After considering all options we settled on repowering and leaving the cosmetics alone. Battle scars. In hindsight a great decision. Insurance paid enough for the cost of repowering because we got stated value back in 2004 after all the work had been done. We still get to enjoy our boat and we're not worried about the scars -- and the wife gets to practice running and docking solo without worrying about learning curve dings.

All of this to say that sometimes simple is best. Maybe do the minimum to bring the V-21 up to par and enjoy it -- and leave the rest of the money in the bank.
 
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