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improvements vs.
I think your decision would be best based on the "market" for your boat. I would suggest looking at listings for boats similar to yours and seeing if they have new engines and/or roller furling in the price range you are thinking of selling yours in. If most boats do, then your boat faces that competition when you go to sell it. If you would get more enjoyment out of the upgrades, go for it.
If most boats like yours do not have roller furling or new engines, forget it.
The basic rule is that you will never recoup your investment. Upgrades help you sail your boat and sell it.
Hope this helps, best of luck in Beantown, a very cool place.
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