The Challenges of Investing in STRs Remotely + The Checklist That Helps You Succeed

Buying and managing a short-term rental from out of state is challenging—but completely doable with the right strategy. How do you choose the best amenities to boost bookings? How do you build a reliable local team? What if guest issues arise and you can’t be there in person?

I recently sat down with Kenny Bedwell of STR Insights on the Cash Flow Positive podcast to tackle these exact challenges. I shared the strategies I’ve used to successfully invest in and operate short-term rentals remotely—without sacrificing guest experience or profitability.

Listen to the full episode here:

🎧 Spotify

🎧 YouTube

But in this post, I’m taking it even further with additional insights and practical steps to help you avoid common pitfalls and set yourself up for success. Plus, I’ve put together a free Out-of-State Short Term Rental Buying Checklist to guide you through the process.

Key Takeaways from the Podcast

1. Researching Local Markets & Guest Expectations is Non-Negotiable

A property can look great on paper but perform terribly if it’s in the wrong location.

✅ Use data tools like AirDNA, STR Insights, and Rabbu to analyze occupancy rates, seasonality, and ADR (Average Daily Rate).

✅ Identify your ideal guests—families, business travelers, outdoor adventurers—and tailor your property to their needs.

✅ Read reviews of similar listings to spot patterns in guest feedback.

💡 Pro Tip: Work with an STR real estate agent who understands the local market, STR regulations, revenue potential, and local guest expectations, and can connect you with great cleaners and handymen.

2. How to Vet and Manage Cleaners & Handymen Like a Pro

Your cleaners and handymen are the backbone of your STR business—hire wisely!

✅ Look for professionals who care about guest experience, cleanliness, and property upkeep.

✅ Always have at least one backup cleaner and handyman to avoid last-minute headaches.

✅ Consider hiring a local house manager to oversee cleanings, maintenance, and guest issues.

💡 Pro Tip: Before hiring, conduct a test clean and provide a detailed cleaning checklist. A spotless home = 5-star reviews.

3. The Top Mistakes Investors Make When Buying Sight Unseen

Buying remotely can work if you follow the right process—but these mistakes can cost you thousands:

🚫 Skipping a detailed video walkthrough – Ensure your agent provides a high-quality video tour with commentary.

🚫 Ignoring zoning & permitting laws – Some investors buy properties only to find out STRs aren’t allowed!

🚫 Waiving inspections – Hidden issues (mold, foundation problems, outdated electrical) can derail your ROI.

💡 Pro Tip: Never waive inspections, even in a competitive market. A bad deal will cost you more than losing out on a bidding war.

4. How to Market Your STR to Stand Out & Maximize Bookings

First impressions matter—your listing photos and descriptions must be top-notch.

✅ Work with an experienced STR designer to create an immersive guest experience both indoors and outdoors. Thoughtful design can increase bookings and justify premium pricing.

✅ Hire a professional photographer and stager. Marketing is not an area to cut corners—high-quality photos and staging help your listing stand out and attract bookings.

✅ Highlight unique amenities (hot tub, game room, mountain/waterfront views, fire pit).

✅ Optimize your listing title and description with guest-focused language.

💡 Pro Tip: Guests book with their eyes! Listings with professionally staged, well-lit photos consistently outperform DIY iPhone photos in search rankings and conversion rates.

6. Why Skipping Inspections is a Costly Mistake

Home inspections protect your investment and negotiation power.

✅ Pay extra for specialized inspections (e.g., swimming pool, plumbing, roof, HVAC).

✅ Attend the inspection in person if possible—or request a detailed video report.

✅ Don’t just review the report—discuss issues with your inspector and create an action plan.

💡 Pro Tip: A $500 inspection can save you tens of thousands in unexpected repairs.

7. Budget Smartly for Amenities That Increase Guest Satisfaction & ROI

Not all amenities boost bookings or justify the cost. Prioritize wisely!

✅ Invest in high-ROI amenities (e.g., hot tubs, fire pits, game room with arcade games, home theaters).

✅ Choose durable, stylish furniture that holds up to frequent guest use.

✅ Factor in ongoing maintenance costs before adding high-maintenance amenities.

💡 Pro Tip: Don’t just follow what competitors are doing. Choose amenities that fit your guest avatar, experience vision, and budget.

Avoid Costly Mistakes with This Free STR Buying Checklist!

Investing in STRs remotely doesn’t have to be risky. With the right strategy, you can build a profitable, well-run portfolio from anywhere.

Invest and manage smarter—while avoiding costly mistakes!

Interested in getting started with Short-Term Rental (STR) investing or elevating your existing rental? Book a free 30-minute discovery call today. 📞✨