5 Tips For Targeting Owner-Managed STRs vs. Owners Using Another Property Manager

As you build a pipeline of prospective rental properties for your portfolio, it’s worth remembering that self-managing owners and owners working with another management company need very different approaches.

January is a great time to target self-managing owners (outside of ski/winter high-peak destinations). After being on-call and available 24/7, 365 days a week handling reservations, guest messages, complaints, reviews, pricing, revenue management, maintenance, customer service fires, on top of managing their lives and careers, the idea to pivot to working with a property manager may have them thinking, “Do I really want to continue doing this next year?” 

The decision to trust an “outsider” to manage their properties doesn’t usually happen overnight - it’s a process. But the opportunity to prove your value is always there. Owners who seem “anti-management” are usually just pro-control, pro-value, and pro-results. 

Here are 5 ideas to earn their confidence:

1. Speak to the burnout (without saying the word)

   Most self-managers don’t think they’re failing—but they’re tired. Your messaging should acknowledge time, stress, and missed opportunities, not mistakes. Show them what lighter ownership looks like.

   
   

2. Be helpful before you try to win the business

   Market data, pacing updates, pricing trends—this stuff helps owners right now. Sharing it builds credibility outside of the discussion about management. And it shows that even if they also have access to data, you are validating and/or adding to their information, along with demonstrating your ability to understand their specific needs and market.

   
   

3. Make the idea of switching feel manageable

   One of the biggest hurdles you’ll hear is a fear of disrupting their business. Clear onboarding, realistic timelines, and flexibility go a long way.

   
   

4. Use real examples, not big promises

   Specific stories, and inviting prospective owners to speak to current owners, can beat big, unsubstantiated claims. What changed for an owner after they handed things off to you? What got easier? What actually improved? 

   
   

5. Stay visible, not pushy

   While owners may not make a move this month - or as quickly as we would like, they’ll remember who showed up consistently and sounded like they understand their business. Build a relationship by staying in touch. This can mean sending occasional articles, local news, and sharing ideas. Or simply inviting them for coffee because the STR community in your market is small and it’s always great to have friends in that community.

January can be a time to plant seeds that turn into signed agreements later in the year. Stay tuned for ideas to approach owners working with your competition.