The Carpetbagger’s Guide to Home Ownership

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Then in October, much to my surprise, I bought a very similar house right across the street from the first one. I’m now employing the same group of local trades to renovate it, as well. If all goes to plan it should be rented by spring to equally qualified and respectable tenants.

In a perfect world I’d much prefer to use my financial resources to build genuinely affordable new housing which society desperately needs. But this isn’t a perfect world. It’s decidedly imperfect. I learned that the hard way. So I’m essentially reaching back into the past and shining up the leftovers from a previous era.

My real estate agent Ben was instrumental in these transactions. Not only did he identify the right properties for me, but he helped assemble a team of trusted trades to upgrade the mechanical systems, paint, install solid wood floors, new appliances, countertops, look after the landscape, and so on. I honestly couldn’t have done any of this without his guidance or the great people he introduced me to. The first project was such a smooth experience that it gave me the confidence to move forward with the second sooner than I might have planned.

Ben recently invited me to be on his podcast on the topic of real-estate investing. I hesitated. I didn’t want to be perceived as the token out-of-state carpetbagger driving up housing costs for locals and pushing up rents. The problem, of course, is I might be exactly that… So I asked if we could take a different approach.

Instead of me talking about my real-estate activities as a comfortably middle-aged guy with some extra cash to deploy, what if we had a conversation about how I first bought property when I was much younger and infinitely poorer? If I somehow managed to buy property in a crazy expensive place like San Francisco on a super tight budget, that might help people in Madison explore their own options in a more moderate economic environment.

There are alternative routes to acquiring real estate for those feeling the squeeze. Being angry at investors or landlords doesn’t get people into the housing they need. Understanding the institutional structures of real estate and exploring creative workarounds just might. I’ve written about my adventures in property before, but the subject matter is worth repeating. These options may not appeal to everyone, but they worked for me.

I’ll start off by saying I’m a housekeeper. I clean other people’s homes for a living. Are we clear on this? I’m a maid. I grew up in an unstable household that limped from crisis to crisis. I dropped out of high school, left home, and moved to the other side of the country. Leaving allowed me to find more fertile soil to plant myself, and my absence meant one less problem for the family to deal with.

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