What happens when NYC properties drop 30-50% in value and investors can buy buildings for less than the debt—and how do you know when a construction boom signals the market top?
In this continuation episode, Dylan Vaccaro reveals how regulatory pressure and investor flight have created unprecedented opportunities in New York City real estate. He explains his "crane theory" for identifying market tops—when you see maximum construction activity in an established city, it's usually time to stop building and start preparing for the downturn. Dylan shares insights about buying properties in bank workout situations, why rent stabilization makes NYC attractive for contrarian investors, and discusses the role of luck versus skill in generational wealth building. The conversation shifts to Angel's mobile home community development in Waco, exploring exit strategies at various completion stages, before concluding with Dylan's AI-powered solution that reduces underwriting time from 2-3 hours to 10-15 minutes.
[00:01 - 07:00] NYC Market Opportunities in Distressed Times
How regulatory pressure drove prices down 30-50% creating buying opportunities
Why Dylan buys most NYC deals under the debt in bank workout situations
The contrarian thesis: when everyone zigs, you should zag
[07:01 - 12:00] Timing, Luck, and Generational Wealth
Why "the worst developers who time the market right will seem like geniuses"
How "the harder I work, the luckier I get" creates opportunities
The importance of staying power through economic cycles
[12:01 - 18:00] The Crane Theory and Development Timing
How maximum crane activity in established cities signals market tops
Why building through recessions can position you perfectly for recovery
The 2008 lesson: when building becomes too obvious, reassess
[18:01 - 24:00] Mobile Home Community Development
Angel's 104-pad Waco project near Amazon facility and top school district
Multiple exit strategies: sell at drawings, roadways, or fully developed
Why resident-owned homes create 10+ year tenancies vs. 18-month park-owned turnover
[24:01 - 26:30] AI-Powered Underwriting Solution
How DealQueue reduces underwriting time from 2-3 hours to 10-15 minutes
Solving the data parsing pain point from PDFs, Excel, and handwritten notes
Why this problem resonates "across the board" from beginners to professionals
Connect with Dylan: https://www.linkedin.com/in/dylan-vaccaro-4450b9140/
Key Quotes:
"The worst developers who time the market right and get lucky in an upscale market will seem like geniuses. But even the best developers in a downward market will seem like a fool." - Dylan Vaccaro
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