I'm curious if you've calculated the cost-per-usage for the sailboat? Have you facepunched yourself hard enough?
You have 2 cars that could go another 100k miles, so the sailboat is supporting its own costs plus the Jeep's costs.
The Jeep probably costs I'm guessing $2,000/year to own if only driven very low mileage for specific uses (liability only insurance, maintenance & tires, gas, registration, property tax, near zero depreciation until it dies).
I don't know what the sailboat costs to own per year, but I'm thinking it needs to be covered with a tarp that wears out annually or a shed that depreciates, the trailer needs tires every 5 years, various repairs will be needed, ropes and sails dry-rot, and then there's insurance and registration. Does $1,000/year sound fair for all these things? I assume you're not paying for storage.
So far we're talking about a $3,000/year hobby to support the sailboat plus the tow vehicle. Divide this number by the times you use the sailboat per year. E.g.
10x = $300 per excursion
5x = $600 per excursion
You are thinking about replacing the Jeep with a vehicle like the 2023 RAV4 Prime SE which
according to the Edmunds TCO calculator will cost $47,032 to own for five years in Hartford, Connecticut. That means your tow vehicle costs have gone from $2k/year to about $9400/year. Add the $1k/year sailboat costs and the hobby has gone from a $3k/year hobby to a $10,400/year hobby.
Of course, the comparison so far is unfair because you'll drive the new SUV the vast majority of the time as a primary vehicle, and will probably get rid of one of your old cars in addition to getting rid of the Jeep. Supposing the old cars also cost $2k/year to own, you can get rid of one of them and reduce the cost of the hobby to $8,400/year.
Now your cost of sailboating per use is:
10x = $840 per excursion
5x = $1,680 per excursion
Would you pay that much in cash to rent a similar boat for a day on the lake/ocean? Does the hobby still make sense at this cost structure, or would you rather take different types of vacations while driving the 2 beater cars another 5 years? If you were allocating an $8,400/year recreation budget and didn't already own any vehicles, would you spend it on an SUV+sailboat or would you spend a couple weeks in Europe or the Caribbean each summer?