10 Common Obstacles Aspiring STR Hosts Face (and How to Overcome Them)

Becoming a short-term rental host can be incredibly rewarding, and getting started comes with its fair share of challenges. I’ve been there myself, navigating the learning curve while always striving to create five-star stays for my guests. Whether you’re dreaming about your first Airbnb or just starting to explore this world, knowing what to expect (and how to handle it) can save you a lot of time, money, and stress.

Here are 10 of the most common obstacles new hosts face, along with practical solutions that actually work.

1. High Startup Cost

Buying a property, furnishing it, and covering initial expenses can feel overwhelming.

How to overcome it:

Start small. Rent out a room in your home, or convert a garage or ADU into a guest space before taking on a whole property.
Partner with someone. Co-hosting for another owner is a great way to get experience and earn income with little to no upfront investment.
Get creative with financing. Use 0% interest credit cards for furniture or look into STR-friendly lending options like DSCR loans.
Read more in my article “30 Proven Ways to Fund Your First Short-Term Rental: From No Money Down to Creative Financing.”

2. Understanding Local Laws and Regulations

Each city has its own rules when it comes to short-term rentals. It’s easy to get caught off guard.

How to overcome it:

Consult a local expert. A real estate attorney or STR consultant can help you stay compliant from day one.
Join local host communities. Facebook groups and Airbnb Community forums are goldmines for staying up to date.
Research proactively. Use platforms like AirDNA or Mashvisor to identify STR-friendly markets before you buy.

3. Finding a Profitable Market or Property

Not all locations or homes are ideal for short-term rentals, even if they seem like a good fit at first glance.

How to overcome it:

Leverage data tools. AirDNA and PriceLabs Market Dashboards help you analyze demand, occupancy rates, and average daily rates.
Look for niche appeal. Properties that cater to families, pet owners, or remote workers tend to stand out.
Test demand first. Try midterm rentals on Furnished Finder to gauge interest before committing to a short-term model.

4. Time-Consuming Guest Communication

Answering questions and coordinating logistics can become a full-time job if you let it.

How to overcome it:

Automate everything you can. Smart Messaging on Airbnb, or tools like Hospitable, can handle most guest communications for you.
Create quick replies. Saved message templates for things like check-in, check-out, and FAQs save time and provide consistency.
Consider a virtual assistant. Even just a few hours a week can make a big difference.

5. Cleaning and Turnover Headaches

Keeping your space clean and guest-ready between bookings is one of the most critical (and stressful!) parts of hosting.

How to overcome it:

Build a strong cleaning team. Have reliable people you trust, and always line up a backup in case someone can’t make it.
Use turnover apps. Tools like Turno or Breezeway help schedule and quality-check your cleanings automatically.
Reward great cleaners. Bonuses or tips go a long way in building loyalty and attention to detail.
Be sure to check out my “Ultimate Short Term Rental Turnover Checklist!”

6. Pricing Your Listing

Getting the pricing right is key. Too low and you leave money on the table, too high and your calendar stays empty.

How to overcome it:

Use dynamic pricing software. PriceLabs, Wheelhouse, and Beyond can adjust your rates in real-time based on demand.
Study the competition. Compare similar listings in your area to get a feel for average nightly rates and minimum stays.
Start low, then scale. For new listings, consider lower pricing to build momentum with reviews, then raise gradually.

7. No Reviews Yet

Guests trust reviews. Without them, even a beautiful listing can struggle to get traction.

How to overcome it:

Do a soft launch. Invite friends or family to book at a discount and leave honest reviews.
Ask for reviews nicely. After checkout, send a warm message thanking the guest and inviting feedback.
Go above and beyond. Small touches like snacks, handwritten notes, and a well-curated guidebook can make a big impact.

Read more in my other article “How to Get Your First Reviews as a New Host (Without Feeling Awkward About It).”

8. Furnishing and Styling the Space

Creating a beautiful, functional, guest-ready home can be a full-time project on its own.

How to overcome it:

Use a checklist. STR-specific furnishing guides help ensure you don’t miss anything important.
Design for comfort and photos. Good lighting, cozy linens, and neutral colors help create a five-star vibe that photographs well.
Hire help if needed. Virtual interior designers or STR stylists can create a plan within your budget.

9. Fear of Bad Guests or Damage

It’s normal to worry about what might go wrong, from noise complaints to broken furniture.

How to overcome it:

Set clear house rules. Be upfront about expectations, and use booking settings to filter guests.
Use guest screening tools. Airbnb’s ID verification and tools like Autohost add a layer of protection.
Protect your space. Smart locks, exterior cameras, and platforms like AirCover or Safely help minimize risk.

10. Managing Finances and Taxes

Handling income, expenses, and tax paperwork can be confusing and time-consuming.

How to overcome it:

Use accounting tools. QuickBooks paired with a STR template or tools like REI Hub can simplify your books.
Track everything. Keep digital copies of receipts, and label each transaction as it happens.
Work with a tax pro. An accountant who knows STR rules can help you maximize deductions and avoid surprises.

Final Thoughts

Hosting is work, and it’s also one of the most fun and rewarding ways to build wealth, serve others, and create memorable experiences. If you’re thinking about starting a short-term rental, know that you don’t have to go it alone. There’s a whole community of hosts (myself included) who’ve been through it and are happy to share what works.

Continue reading on another article, “Why Rental Properties Are Still the Best Way to Build Wealth: From a Realtor & Real Estate Investor.”

Got questions? Drop them in the comments or connect with me on Pinterest or Facebook @KP_BNB. I’d love to help you get started.

Here’s to 5-star hosting!

– KP