On this week’s episode of Short Term Rental Management, Luke sits down with David to unpack his journey from a full-time engineering career to owning six short-term rentals and managing more than 35 units for other investors. David shares how he leveraged disciplined investing, systems, and team building to scale, why pricing and operations matter more than hype, and what it really takes to leave a W-2 job for long-term freedom through real estate. The conversation dives deep into property management realities, software stacks, staffing, and why adaptability and honest pricing are essential in today’s STR market.

How to connect with David:


Website: https://shorttermconnections.com


Direct booking brand: https://865vacations.com


Instagram & TikTok: @865Vacations



How to connect with Luke:
The Short Term Shop - https://theshorttermshop.com/
Short Term Shop Plus - stsplus.com
Follow us on Instagram 
Follow us on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube
 
For more information on how to get into short term rentals, read Avery’s books:
Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

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