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In 2012, I bought the least expensive house (in a reasonable condition) that I could find in the most expensive zip code in the area. I like the neighborhood and the house is comfortable but this is my front yard. Over the years, I have thought about upgrading to something more. I have also thought about buying a condo in Mexico and spending part of the year there in hopes of eventually getting dual citizenship. After all, Mexico City is in the same time zone as Milwaukee. ...

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... That would make working remotely pretty easy. With my house at the back of the lot and the neighbor's house at the front of the lot, I have started thinking about the idea of building a new house in the front yard and then having the current house declared an ADU by the city. I could build the house of my dreams in a neighbourhood that I like, rent the old house out to offset the cost, and hopefully come out the other end without too much pain. ...