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Get Paid For Your Pad | Airbnb Hosting | Vacation Rentals | STR Revenue Management

How to Invest & Crush It in Competitive STR Markets

Ep. 310

Airbnb Superhost Rebecca Cramer lives by the philosophy that it’s better to regret something that you’ve tried than to regret something that you didn’t try at all. And that attitude has served her well, inspiring Rebecca to invest in short-term rental (STR) properties in highly competitive markets and absolutely crush it—proving that big risk, when done right, can reap big rewards.


Rebecca is the founder of Mad Men Vacation Rentals, a STR business with listings in Maryland and Florida. She invests in vacation spots she and her family love, creating the Mad Men Beach House listing in Ocean City, MD, and the Mad Men Magic Kingdom House near Disney World. Rebecca started hosting on Airbnb in January of 2018 and has quickly proven that newcomers can be successful in crowded STR markets.


On this episode of Get Paid for Your Pad, Rebecca is back to discuss her decision to invest in competitive locations like Maryland and Florida. She walks us through the process of finding, buying and renovating STR properties, explaining what she did to research profit potential and why her listings surpassed expectations. Listen in for Rebecca’s insight on furnishing your STR (without breaking the bank) and learn her top strategy for getting more bookings in the off-season!


Topics Covered


Rebecca’s STR portfolio

  • Start with Ocean City vacation home in 2018
  • Added Disney World property last year
  • Deep Creek Lake location will go live in 2020


How Rebecca found the Ocean City property

  • Discovered neighborhood on vacation there
  • Outdated house on Zillow (9 months on market)


How Rebecca researched STR profit potential in Ocean City

  • Look at similar listings in neighborhood on Airbnb
  • Talk to realtor, friends with vacation homes there


Why Rebecca’s listing surpassed profit projections

  • Renovations, updated furnishings and amenities
  • High level of customer service


What Rebecca did to command a higher price for her listing

  • Offer kayaks, pool and tennis courts
  • Made property dog friendly


How well the Ocean City property performed

  • Covers mortgage, updates and cleaning fees
  • Provide down payment for next investment


Why Rebecca chose to invest in Florida

  • Open to risk, confident in ability to recreate success
  • Family loves Disney + can escape there themselves


How Rebecca furnished her listings for less

  • Sold furniture that came with properties
  • Utilized Craigslist, Facebook Marketplace
  • Willing to paint/refinish distressed pieces


Rebecca’s strategy for getting more listings in the off-season

  • List property twice (e.g.: 3BD/2BA AND 1BR/1BA)
  • Fill booking gaps with solo travelers + small groups


Connect with Rebecca

Mad Men Vacation Rentals

Mad Men on Instagram

Mad Men on Facebook

Mad Men Beach House

Mad Men Magic Kingdom


Resources

Rebecca on GPFYP EP309

AirDNA

STR Profit Academy

STR Legends Mastermind

Email jasper@getpaidforyourpad.com


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    34:53||Ep. 697
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    24:45||Ep. 696
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    42:48||Ep. 695
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    21:09||Ep. 694
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    34:27||Ep. 693
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    23:11||Ep. 692
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  • 691. The One-Goal Method: How to Win 2026 by Doing Less

    32:47||Ep. 691
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  • 690. The Real Revenue Opportunity Behind “Small” Holidays

    22:42||Ep. 690
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  • 689. From Hurricane Loss to 70 Rentals: Scaling STR Business

    32:09||Ep. 689
    👉 Get a Free Revenue Review → https://www.freewyldfoundry.com/reportFind out how much money your portfolio is leaving on the table. Risk-free.What happens when a hurricane wipes out one-third of your short-term rental portfolio in just two weeks, and forces you to rethink everything about how you operate, scale, and survive?In this episode of Get Paid For Your Pad, Kaye Putnam (Head of Marketing at Freewyld and Freewyld Foundry) sits down with Joe Prillaman, co-founder of Host Help, to unpack how a natural disaster became the unexpected turning point that pushed him from managing his own properties to building a professional STR management company overseeing nearly 70 homes.Joe shares the raw reality of losing properties to hurricanes and floods, carrying fixed mortgages and team costs, and realizing that managing for owners is a completely different business than managing your own portfolio. This conversation explores the operational stress, leadership decisions, and system-building required to rebuild stronger—without sacrificing guest experience, five-star reviews, or long-term vision.Whether you manage 10 listings or are already scaling a full property management operation, this episode offers a clear look at what actually breaks as portfolios grow, why quality must be built upfront, and how crisis often accelerates the lessons most operators learn too late.You’ll discover:• How losing one-third of a portfolio forced a major STR business pivot• Why managing owner properties is far harder than managing your own• What changes operationally when you move from 30 to 70 rentals• Why “cute, clean, comfortable” still drives five-star reviews at scale• How guest experience systems prevent small issues from becoming disasters• Why quality onboarding saves years of operational pain• How pricing becomes the highest ROI activity once systems stabilize• Why removing ego is essential as teams and portfolios grow• How disasters expose weaknesses most operators overlook• What it really takes to scale STR management sustainablyJoe and Kaye also explore how hurricanes and floods reshaped Host Help’s risk management approach, why disaster preparedness must be built into STR operations, how AI is reducing daily workload without replacing people, and why most operators underestimate the staffing and systems required to scale beyond survival mode.💡 Topics Covered:• STR portfolio loss and crisis-driven growth• Scaling short-term rental management companies• Guest experience systems and five-star reviews• Onboarding processes and operational checklists• Pricing strategy as a leverage point• Leadership roles and team structure• Disaster preparedness for coastal STR markets• AI in guest communication and operations• Seasonal profitability in beach destinations🔗 Relevant Links:Learn more about Freewyld Foundry → https://www.freewyldfoundry.comFollow Kaye Putnam → https://www.linkedin.com/in/kayeputnamFollow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundryKeywords:airbnb, short-term rentals, STR property management, scaling STRs, hurricane disaster, STR portfolio loss, vacation rentals, property management systems, guest experience, five-star reviews, STR operations, revenue management, pricing strategy, AI in hospitality, coastal rental markets, STR growth, Freewyld, Freewyld Foundry, Get Paid For Your Pad, Kaye Putnam, Joe Prillaman, Host Help, vacation rental management, scaling property management businesses