I’ve wondered why you would want to spend a ton of money on a home that you will need to upkeep, and you will feel like you need to keep going to that same place over and over to make it worth it, when you could instead go to nearly any vacation home or resort basically as often as you’d like for a fraction of the cost, and not need to worry about upkeep. Just show up and everything is made ready for you.

Maybe you could use it as an investment, but I’ve heard it can be a challenging investment and, not ideal to use as a personal vacation home when trying to make money on it.

Say I’m in a position to purchase a vacation home in the future. What are the reasons I should do so?