The Getting Started Playbook for New STR Owners: From Contract to Cashflow

Kate Stoermer Author

Hints and Tips for your new STR biz

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Congratulations on stepping into the world of Short-Term Rentals (STRs)! Whether you’ve just gone under contract for your first rental property or decided to convert your current property into an STR, the journey from here is exciting - but can also be overwhelming. But don’t worry, I’m here to walk you through the essential steps from setup to operations and marketing to backend management, ensuring your venture into STRs is both profitable and enjoyable.

1. Setup: Designing Your STR for Success

So once you have - or are under contract for, a property the key next steps is to plan out your setup phase!  Set up is crucial and should be approached with your end goal in mind. Are you creating a lifestyle asset for personal enjoyment that occasionally rents out, or is this a pure investment property? Your target audience will dictate how you furnish and equip your space.

Lifestyle Asset: If the property is mainly for personal use, tailor it to your tastes and needs. However, remember that personal touches should be adaptable for occasional renters, and do keep guests in mind. 

Investment Property: Here, every decision from wall color to appliance selection should appeal to your ideal guest. Research similar successful properties in your market to understand trends and expectations. Think durable, stylish, and highly functional.  People don't always treat your property as theirs; commercial-grade properties, easy care fabrics, and  touches that will appeal to your audience are key.  

2. Operations: Streamlining Daily Management

Operating an STR requires many different operational areas.  

Day-to-Day Management: Decide whether you will manage the property yourself or hire a property manager. Self-management can be more hands-on and personal, but a good property manager can save you time and stress.  While self-management **can** "save money", I always council clients to consider what their time is worth - and is it better focused on other money making activities than the work required not only to manage operations, but also to learn how to do it well, to learn the software, how to optimize, stay on top of the market.  Its a job, so consider that decision carefully.  Day-to-day management is guest communications, coordinating services, maintaining supplies and responding to any property issues. 

Cleaning and Maintenance: Establish reliable processes for housekeeping, laundry, and ongoing maintenance. Consider hiring professional cleaners to ensure high standards. Set up a regular maintenance schedule to address wear and tear before it becomes a significant issue, or have ensure clarity with your property manager who is responsible for what.

Inventory Management: Keep track of all items in your rental to ensure that nothing is missing or damaged after guest stays, and ensure to do walk throughs to assess needed replaces, upgrades, and helpful amenities.  Regular audits can help maintain the quality and readiness of your property.

3. Marketing: Maximizing Visibility and Bookings

Effective marketing is key to keeping your STR booked and profitable and requires regular focus. I personally touch all my listings at least 2x a week with marketing as the goal; if you choose to take this on you will find a cadence that works for you but it needs to happen regularly.  Marketing includes; 

Listing Optimization: Your online listing is your property's first impression. Check out my course on Listing Optimization to learn how to create compelling listings that convert browsers into bookers.

Direct Bookings: While platforms like Airbnb and VRBO are great, direct bookings can save you from hefty platform fees and give you more control over guest experiences.

Social Media: Use platforms like Instagram and Facebook to showcase your property’s unique features and local attractions. Engaging content can drive direct bookings.

Pricing Strategy: Dynamic pricing tools can help you adjust rates based on market demand, local events, and seasonal trends. Stay competitive by understanding your market and adjusting prices accordingly. That said, pricing is merely a tool and conveying the value offered is the more important job of marketing.  

Reviews: Getting - and giving, great reviews is a marketing activity.  Not only do we want to deliver a great guest experience, but to have that guest leave us a review. There is no more helpful tool in our marketing tool box than to have social proof that staying at our property is a top-notch experience. 

4. Backend: Laying the Financial and Legal Foundation

Setting up the backend of your STR business is as crucial as the guest-facing elements:

Financial Management: Set up a separate bank account for your rental business to track income and expenses accurately. Consider software solutions for bookkeeping and financial tracking. Routine activities during set up will be maintaining all receipts and reconciling accounts.  You'll be paying venders and, as your property gets up and running - tracking income as well.  

Legal Structure: Consult with a lawyer to determine the best legal structure for your STR business. This could be often an LLC, but for some an S corp or other structure may be appropriate to optimize tax benefits and legal protection.

Regulatory Compliance: Ensure you are compliant with local STR regulations, zoning laws, and tax obligations. Failing to do so can lead to fines or shutdowns. I tell my clients to at least quarterly reassess the regulatory climate unless you are in a very mature STR market.  I've seen too many clients surprised by new ordinances put into place; its not the townships job to notify you.  Read minutes or attend local township meetings to stay on top of any regulatory changes and to be at the forefront if it does arise. 

Insurance: Obtain the right insurance coverage to protect against property damage, liability, and loss of income. Standard homeowner's insurance does not cover STR activities.  Further, damage insurance may be a great option - I personally use Waivo to avoid having guests contacted (and thereby potentially leaving a less than stellar review) 

5. The Ramp Up Period

Go live is a critical time period, but its not a time period to think your bills will just start being covered.  A critical aspect of STR is understanding the market, how it cycles, and how to minimize your ramp up period.  I bought most of my properties in off season - at the tail end of high season which meant I both had time to set up - but also needed to have the funds to carry the property financially through given in my markets, 80% of my annual income is generated in a 2.5 month period.  The ramp up period is critical, as is the timing of "Go Live".  I ALWAYS recommend using the "new listing" discount on the booking platforms - if you work with a property manager, they will undoubtably be and if you self manage - you should too. The ramp up period is a time to get reviews as fast as you can.  Why? Because social proof goes a long way to getting listings - and you'll get promoted on the booking platforms as well.  The algorithms won't push your listing until you are more established. So understand that as you get going, "Go Live" isn't the end - its the beginning.   

Set up to go live is often a big push, especially if you are new to short-term rentals. Its okay to take it in stages and aim for progress - not perfection. 

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Hey Boss! I'm Kate, owner/founder of The CEO Host. If you are interested in taking a leap into short-term rentals - or have some questions about your existing business, my goal - passion, and career, is to help YOU succeed. I've coached hundreds of folks getting started or looking to optimize, analyzed more deals (and duds) than I could count, completed thousands of hours of education and training, attended conferences... So don't be shy. A good CEO knows to bring in expert help - and that's what I'm here for! Lets HOP ON A CALL and chat!