🎙️ Welcome back to another eye-opening episode of The Physicians and Properties Podcast with host, Dr. Alex Schloe.

💡 What if your path to financial freedom wasn’t choosing either active real estate or passive syndications—but designing a portfolio that uses both for cash flow, tax efficiency, and time freedom?

In this episode, Alex sits down with Dr. Chirag Chaudhari—an emergency medicine physician and multi-asset investor with holdings across multifamily, short-term rentals, hotel-to-multifamily conversions, land, oil & gas, and preferred equity. Chirag unpacks how he used 1031 exchanges to scale, why he chose Clearwater STRs (hello, mother-in-law + legitimate write-offs), and how he now co-invests in institutional deals—bringing physician capital together to negotiate better terms and de-risk execution.

From the short-term rental tax loophole (with material participation and cost seg) to energy deals that can offset active W-2/1099 income, this conversation is a blueprint for physicians who want freedom to practice medicine because they want to—not because they have to.

🔥 What you’ll learn:

• Active → Passive playbook: How an ER doc grew from LTRs to STRs to 20+ LP syndications
• 1031s, simplified: Rolling equity from a paid-off $150K LTR into a $600K Clearwater STR—without paying taxes on the gain
• STR tax advantages: Material participation + cost segregation = potential six-figure paper losses against clinical income
• Oil & gas 101: IDC credits, targeting 80–90% first-year deductions on W-2/1099 income, plus front-loaded cash flow
• Hotel → Multifamily conversions: Inside a 787-unit studio housing project in Olympia, WA
• Land deals for growth: Why some investors trade cash flow for 3–5× equity multiples in 3–5 years
• Co-investing edge: Pooling capital via an LLC to win better splits, lower mins, and cleaner investor relations
• Diligence that protects you: Vetting sponsors > vetting deals; background checks, third-party feasibility, sensitivity analyses

🔥 Key Takeaways:

• Freedom is the goal; real estate and entrepreneurship are the vehicles.
• Compress timelines with education, masterminds, and community (borrow belief until you have your own).
• The sponsor is the jockey—bet on them first, then the deal.
• Mix assets for resilience: STR cash flow, land appreciation, energy tax benefits, and institutional ops.
• Use the code legally: 1031s, bonus depreciation, STR material participation, IDC credits.

⚠️ Friendly reminder: none of this is legal, tax, or investment advice. Always consult your CPA and attorney (preferably with real estate and cross-asset experience).

🔗 Connect with Dr. Chirag Chaudhari:

• LinkedIn
• Website

If you want to learn how investing in real estate can give you the freedom to practice medicine and live life how you want then check out the links below:

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