Jay Sudowski brought an unconventional background to vacation rental management: running critical IT infrastructure for Denver's transportation system and school districts. In 2022, he bought Beachside HHI in Hilton Head, South Carolina with just thirteen properties while simultaneously selling his tech company and training for a half Ironman. Three years later, he's nearly doubled the portfolio to thirty properties while maintaining an ultra-lean team of three full-time staff. In this episode of The Vacation Rental Show hosted by Lynell Gordon, Jay shares why managing vacation rentals feels easier than keeping payment processing systems running for hundreds of thousands of transit users, how his three-bedroom property 0.6 miles from the beach grosses one hundred ninety thousand dollars annually, and the hard lesson he learned about firing homeowners who don't align with brand standards regardless of their revenue potential. Jay discusses achieving forty-five percent direct bookings in Hilton Head's traditionally Saturday-to-Saturday market, why inland properties dramatically outperform oceanfront homes on ROI, and his systematic approach to growing slowly enough to maintain quality with current tools and team. This episode is sponsored by Streamline.