I wonder what it would be like to be so rich that I could afford to pay taxes, insurance, upkeep, maintenance, and utilities on two places for 12 months a year, especially when one of them is only being used three or four months a year -- that is expensive upkeep even if the mortgages are paid in full.
For years, I comtemplated where to buy a second home and have been so glad I could never make up my mind. With what I'd be spending every year on keeping a second home, I am able to travel freely for up to five months a year. And that doesn't even include the original outlay of money to buy a place!!