Can't speak personally to yacht ownership. I do know that Irma and Covid were hard on yacht and house owners, with uninsured losses from damage and missed revenue. Some charter companies stopped paying out on guaranteed revenue contracts, leaving owners to pay their notes. Search here and you also will find owners who've had to fight with charter companies to get damage caused by others repaired.

For a young family, it may be worth hooking up with a good owner and buying their time.