Lessons Learned from Our First STR Setup

I am famous within my own family… actually, let me rephrase… I am infamous within my own family for underestimating the time and resources needed to complete a task. Transforming a 30-second diaper change into an epic saga requiring several minutes and an arsenal of baby wipes, or turning a 25-minute meal prep into an hour-long ordeal with an emergency grocery run, are just a couple of examples. Among my most ambitious misjudgments involved building a shed with my old man, where a projected one or two-week endeavor morphed into a two-month saga.

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This tendency of mine has never been more apparent—some would say problematic—than in setting up properties for short-term rentals (STRs).

Our inaugural STR venture seemed straightforward: clear out the clutter, renovate, furnish, and voila! DONE!

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Right?

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Wrong! Reality had other plans. The property came with the previous owner’s unwanted furniture, and a non-negotiable part of the sale during a seller’s market frenzy. Our initial step was to rid the house of its musty furnishings, outdated dishware, and myriad oddities, including a hidden stash of Mike’s Hard Lemonade that the seller’s teenage son had forgotten to drink.

Thanks to a friend's church ministry, which gladly hauled away the furniture for donation, we tackled the first hurdle with ease. The rest of the clutter, however, proved more formidable.

As my wife, Mary, and I stood there surveying the situation, I thought the words “one trip to the dumpster should do it” came out of my mouth. Mary, significantly more perceptive than I, rolled her eyes. “Okay, maybe two,” I allowed.

She rolled her eyes harder.

Nine truckloads later, after a grueling day and countless stairs in a four-story home, Mary’s skepticism proved well-founded. Our legs smoked, our spirits nearly broken, we collapsed at the end of the day. “One trip?” Mary whispered as we lay in bed. I fumbled for a witty reply but only managed a “whatever!” as my lame defense.

The renovation phase was smoother, paving the way for us to focus on furnishing and setting up a spacious 4-bedroom, 5-bath property. Here again, my estimations fell short. Having grown accustomed to the military’s efficient moves, I naively anticipated a single weekend would be enough for Mary and me to get everything in place.

I had suggested to Mary that we would need one weekend for the two of us to load the trailer, drive the 4 hours up the mountains, unload, unbox, build, dispose, finish setup, and return home. 

Cue the eye roll!

That first weekend was a blur of caffeine, cardboard boxes, dumpster runs, and stairs upon stairs. Each day we worked well into the night with pizza in one hand and wine in the other while building furniture, moving items, hanging artwork, and hauling out trash. Three weekends and several weekdays later, we were finally done. I think we made 37 trips on what we now call the “At Home - Lowes - Target - Starbucks” loop. Well, maybe not that many, but it was certainly a lot!

This whirlwind of activity—fighting, laughing, working, and sometimes just silently pushing forward—eventually culminated in a moment of pride as we surveyed our finished product.

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Reflecting on this journey, I’d like to offer some advice for tackling a new property setup:

1. Double or Triple Your Time Estimates: Everything takes longer than you’ll expect. Inevitably you’ll discover that the one allen wrench that is missing from your set is the exact one that you have to have to finish putting a bed together. Or you’ll be 4 inches short of the picture hanging wire you need. Or the bathmat you bought from Target just doesn’t work in that space. Something will go wrong and you will need margin to account for it.
2. Incorporate Break Time: Mary and I learned the hard way that non-stop work leads to burnout and diminished creativity. You can only grind for so long before you become cranky and lose your focus. In that condition your creativity and stamina can evaporate like a morning dew. Nowadays we like to allow ourselves the freedom to get outside for a bit. A walk by the river, for example, will do wonders for the soul and leave you feeling reinvigorated to keep making progress.
3. Consider Outsourcing: I once spent 4 hours building a single dresser, and I consider myself pretty adept with a set of tools. I have since learned that paying someone $20-50/hr to build furniture is a great way to accelerate a property setup. How do you find someone? Just ask! We have had success asking our realtor, our cleaner, and posting in local Facebook groups.

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Navigating the challenges of property setup can be daunting, but with the right approach and mindset, it’s possible to emerge successful—and maybe even with a few laughs along the way.

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Here’s to efficient setups and successful listings!

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