This is partly wishful thinking, as we don't travel nearly as much as we did pre-kids. But I feel wistful about the idea of visiting another place repeatedly so that it feels like a second home.
I once knew a British bloke who spent about four months per year in the same town in India (I think this was for work), and the rest in the UK, so he really got to know the town and the locals. I've also heard of people who visit the same village in Italy every year, or the same village in Cornwall. If you do that, how does it work for you? Do you feel as though you almost get to live two lives, or do you just feel like a tourist who has the convenience of knowing where everything is in your holiday area?
I also knew of a family who made a rule to never to repeat a holiday and to go somewhere different every time, and that's pretty much how our holidays have been. But I'm wondering if we're missing out by not making any deeper connections with another place and its people.