The Robin Hood Resort Story with Christian Osgood

What this episode covers

Most real estate stories focus on the wins. This episode is different. Christian Osgood joins Dave Dubeau to share the full story behind the Robin Hood Village Resort deal that nearly cost him everything. Christian explains how he went from buying duplexes to acquiring a historic resort using seller financing and partnerships, only to discover major operational problems after closing. The conversation covers hidden payroll issues, failed business plans, difficult partnerships, and the massive effort required to rebuild the property into a successful event driven resort. Christian also shares how creative financing helped him scale to more than 600 units and why solving difficult real estate problems became his passion. Key Topics Discussed Buying a historic resort with seller financing Hidden payroll and bookkeeping problems Why multifamily underwriting failed for hospitality Partnership mistakes and cash call problems Turning the resort into a music and event venue Scaling a business to survive a bad deal Lessons learned from creative financing The launch of Christian’s new book on creative real estate Guest Information Christian Osgood Instagram: Christian Osgood Instagram YouTube: Multifamily Strategy YouTube Channel Book: The Book on Creative Real Estate on Amazon Call To Action To connect with Christian or learn more about creative financing strategies, reach out through Instagram, YouTube, or his new book.

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Frequently Asked Questions

How long is this episode of Property Profits Real Estate Podcast?

This episode is 25 minutes long.

When was this Property Profits Real Estate Podcast episode published?

This episode was published on June 18, 2026.

What is this episode about?

Most real estate stories focus on the wins. This episode is different. Christian Osgood joins Dave Dubeau to share the full story behind the Robin Hood Village Resort deal that nearly cost him everything. Christian explains how he went from buying...

Can I download this Property Profits Real Estate Podcast episode?

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