So far everyone seems to be assuming you mean renting or owning gear. As I read it, you are talking about renting or owning a place to live. Is that correct?
I go to Florida every winter for a long term rental--this year it will be two months. My wife and I have talked about owning instead--one of the reasons we go there is because her sister owns a seasonal condo nearby. We enjoy visiting her there, and many of her friends have become our friends, too. We see the attraction. Our discussions about owning v. renting, however, have concluded with renting as our best option.
Our decision is colored in part by the fact that we spent several decades as part owners of a cabin on a lake that we inherited. I loved the place--I hated being an owner. Here's why:
1. In our case, it was much more expensive to own it than to rent it. In fact, the taxes we paid on it each year were more than it would have cost us to rent a similar place at the same location. You would have to do a comparison of the relative costs for your situation. (The value of the property also depreciated during the time we owned it, so there was no benefit there.)
2. My wife and other relatives enjoyed the visits more than I did because most of the time they were lolling in the sun or sailing on the lake, I was doing the annual maintenance on the cabin. I spent most of each vacation doing home repairs. I have been to a lot of rental properties, and not one has expected me to take care of the leaky plumbing.
3. Owning that property greatly limited our vacation options. In order to justify the cost of owning the place, we had to vacation there every year. I actually started a thread on this topic a while ago. Some people own places in dive sites like Bonaire, Curacao, Cozumel, etc., and they delight in going back there year after year after year after year after year after year after year. That would kill me. I want to go to new places and see new things. Right now some friends, my wife, and I are starting to plan a trip to Bali, as a followup to our delightful trip to Australia last year. We would be doing neither if we owned a place somewhere else.
Those are the things I would weigh out if I were you and were making that choice.