How I Acquired My Short Term Rental: Part 2

Pre-arrival Prep, the Visit, and Go-live

In Part 1 of this series, I mentioned that all of my short term rental preparation took place from states away in Colorado. While that’s mostly true, there was one exception; the 6 days when I traveled to Savannah to see my house for the first time. Here in Part 2, I’ll dig deeper into the planning that took place before arriving, build my team, furnishing the home and then later setting it live on AirBnB.

Preparation: the homework assignment of a lifetime

During my home search, I often found myself waiting. I’d be waiting, then randomly get a notification of a new listing, quickly input the numbers into my spreadsheet, text my realtor or realize I didn’t have a deal on my hands. Then I would go back to waiting. There was, relative to the search, a lot of downtime.

The downtime turned out to be advantageous in the long run because it allowed my anxious brain to refocus elsewhere. Afterall, there were a lot of next steps to noodle on like finding a property manager and furnishing the home.

While deciding on this particular strategy (STR investing), I embraced hiring a property manager to oversee the rental locally. I’d factored the expense into my earliest calculations because a) I couldn’t adequately handle the responsibility from states away and b) I wanted this investment to have a scalable foundation. It had to be self-sufficient and profitable, requiring as little of my time as possible, particularly after launch. As such, I would unquestionably need a trust worthy and diligent property manager.

Scouting began with a review of all active local property management companies, detailing the areas they serviced, their fees, and what they offered for homeowners. I found that only a small handful managed homes in the unincorporated areas of the county where regulations were easier to comply with for out of state investors. Later, I interviewed these candidates and sought their opinions on specific homes. One in particular was willing to swing by different addresses, get a feel for the curb appeal and list nearby attractions. As you can imagine, we built great rapport and I came to trust his opinion, eventually hiring him before I even owned a home. 

In parallel, I endeavored to understand the process of furnishing a rental. Browsing online resources, I consumed checklists, recommendations for must-haves, and introductions to companies who would furnish an entire home for you, concluding that I could absolutely handle the project myself if I was organized. I made a new spreadsheet, assigning each room its own tab, listing specific items based on the room’s purpose. Then I located a URL, price, and shipping time from an online store. The end result was a checklist, budget, and delivery schedule. Estimated ship-by dates informed my order-by timeline, allowing items to be delivered around the same time I would arrive at the house. This was much more feasible on paper of course but the initial research shaped my understanding of the true cost of furnishing as well as the level or effort to coordinate numerous deliveries.

My checklist of all necessary items for a functional short term rental.

My 155 item list served as both a checklist and a budget when furnishing the 3 bedroom, 2 bath home. The Cost column helped shape an estimate of total expenses to furnish but thanks to Facebook Marketplace, garage sales and local thrift stores I was able to save on kitchen items, decor, and a handful of large items like rugs. Download my template for free here.

These mini projects took the most amount of preparation but other things brewing in background included arranging travel to Savannah, building a secondary list of items I would purchase in the city upon arrival, and looking for a handyman.

Boots on the Ground: 6 days to operationalize

My original plan was utopian, based on the idea that with enough preparation, everything would proceed smoothly. I’d fly in and my pre-ordered Amazon mattresses would be awaiting me at the front door. I’d unpackage them and spend my first night without a bed frame, compromising to build it on day two while all other items showed up or were available at local stores, and then furnish the entire 3 bedroom home in a mere three days.

My sane family convinced me out of this idea and unsurprisingly, they were spot on when we showed up to a dirty house where no packages had yet arrived. The house was deeply in need of a broom and some 409 and so day one consisted of serious cleaning. We also hired a local handyman to make small repairs and quick cosmetic updates. As he worked through a task list, we traveled from Home Depot to Costco to HomeGoods to collect additional decor.

These days started around 5:30 am and wrapped up around midnight consistently for three days, leading to an extension of the trip when there was still too much to do. Packages were arriving late or containing the wrong item necessitating a pivot in our plan almost every hour.

On multiple occasions I would find myself thinking “how in the world did we get so lucky?” like when we found a $400 rug on Facebook Marketplace for $40, randomly met a landscaper to add to the team, or got the very last mattress cover on the shelves in the local Target. The days flew by so quickly that I can’t even recall everything we accomplished. But by the end of that week, we had fully furnished a three-bedroom, two-bathroom home.

Perhaps my greatest learning during this time was how to be adaptable in the face of a new environment, especially when it came to what I believed to be the easy part of assembly.

Going Live: compliance and finishing touches

The final pitstop before heading home was to the county building to clear up lingering questions about the short term rental application process. Somehow, and I still can’t explain it today, I completely overlooked the potential complexity of this piece of the puzzle.

I was quickly educated that the application was not, in fact, an online form but instead consisted of a 30 plus physical pages, requiring a combination of personal information as well as proof of ownership, insurance, parking instructions, property management, etc.. Every detail needed to be handwritten, signed, notarized, or printed from an online resource.. My heart sank as I realized the amount of time I’d need to complete this knowing the countdown until my first mortgage payment had already started.

Some portions were simple to collect; paying and printing a receipt for local fire services or photocopying my drivers license. Others were much more difficult, such as the private employer affidavit that needed notarized signatures from both me and the property manager, who were now thousands of miles apart.

I have to take ownership here for my failure to properly understand the extensive application process but I paid the price in the form of time and money. It took me nearly 30 days to snail mail documents back and forth from Colorado to Georgia and then to get my 3/4 inch thick completed application back to the county. Their approval similarly moved at a turtle’s pace but on a positive note, it gave us time to order professional photos and build the online listings.

Eventually, I received approvals from every direction, and the Airbnb listing went live. In a matter of days, guests had booked the new home and would be walking into the freshly decorated living room.

This property has been an adventure ever since it’s inception. Even today, it keeps me on my toes. For a glimpse into it’s first rager and other facepalm moments, check out my interview on the Real Estate Rookie podcast with Ashely Kehr and Tony J. Robinson from BiggerPockets. In finality, I would summarize that I learned an immense about myself as an investor throughout this process. As I consider my next investment, I’ll remember that preparation is invaluable and critical for efficiency; however, we’ll never be able to anticipate everything. Always be ready to problem solve as challenges appear. Good luck!