In some ways it often sounds like you are "living the dream" after many years of hard work and financial investments that have paid off. Who wouldn't want to be able to fly to any of those places, drop in for few days, with nothing much to worry about or figure out, right?
But I wonder -- as you alluded to a bit at the end -- do you ever feel like with being split between so many places that none of them are your home base? Do you ever feel like you're missing out on building community long term, vs having friends and communities so spread out that you're not in town when interesting things happen? Or you go too long between visits to really keep those connections alive?
I hope that makes sense. I can see the opposite viewpoint, where with so many homes around the world you have access to culture and opportunities that you wouldn't if you lived in just one place. But I wonder what you think the downsides of this are for you?
I ask because I used to travel a lot, and move around a lot, but now I really appreciate living in one place and focusing on building my life around that -- planting a garden, renovating my house, and doing things where the payoff isn't days or months, but years or decades.
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Back to the full conversationHmm.Chicago’s cultural scene—museums, intellectual communities, vibrant neighborhoods—is truly underrated. the issue is: I’m concerned by the surging taxes tied to massive, underfunded pensions. Powerful unions run the city; but they make NYC look well run...BtW thoughts on Honolulu for living? Is it Overplayed?

Vegas very much feels like THE home base. It's where I always return to after other trips and I'm never gone for very long (1 month feels long, 2 months may be the absolute max I'm gone). Sometimes I spend over a month here with no travel.
My friends are very spread out though, and I'm absolutely missing something by being in the same place as my friends all year round. The cost is worth paying for the incredible upside, but yes, it is a cost.
The reason I buy all of these places is because each one feels like home in a way hostels/hotels/airbnbs didn't. Travel was amazing at first, but after a while I felt like I was missing out on more than I was gaining. Now I don't feel that way at all.