We Sold Our Airbnb Property - And Don’t Regret It (Here’s Why) Sean Bakhtiari

What if the smartest move in real estate isn’t buying more… but selling at the right time? In this episode, we do something most investors avoid — we talk honestly about letting go . They share the real reasons behind their decision to sell one of their short-term rental properties and unpack the uncomfortable questions every investor eventually faces but rarely discusses. Joined by their friend and trusted real estate advisor, Sean Bakhtiari , the conversation dives into when selling actually makes strategic sense — from struggling cash flow and high-interest DSCR loans to changing life priorities, market shifts, and the power of unlocking trapped equity. Sean explains how solid bookkeeping, clear goals, and objective advice can transform an emotional decision into a smart long-term move. They also explore lifestyle-driven markets like Provincetown, Hampton Beach, and Salisbury Beach , the realities of self-managing vs. co-hosting, and how successful investors think not just about growing a portfolio — but pruning it when necessary . If you’ve ever wondered “Should I hold, or is it time to sell?” — this episode is for you. Things we discussed in this episode: Why and when to sell a short-term rental rather than hold forever. Jason & Rory’s decision to sell their Gillford, NH property , including emotional and financial factors. Impact of high-interest DSCR loans and debt service on cash flow. The importance of good bookkeeping, clean P&Ls, and separate bank accounts for each property. Common reasons owners sell: poor cash flow, operational issues, market shifts, or lifestyle changes . Selling when a property has significant equity and considering redeploying that capital elsewhere. The role of lifestyle markets (e.g., Provincetown, Plum Island) vs pure investment markets. Sean’s thesis on emerging value in Hampton Beach and Salisbury Beach as future winners. When co-hosting / professional management makes sense vs when owners should self-manage. Sean’s community-focused approach with The Bakhtiari Group and his partnership with Seacoast to Summit Vacation Rentals. Get in touch with SEAN : Facebook - ⁠⁠⁠⁠⁠⁠⁠ Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Instagram - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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We Sold Our Airbnb Property - And Don’t Regret It (Here’s Why) Sean Bakhtiari is an episode from The Real Estate Law Podcast by Airbnb Superhost Jason Muth + Rory Gill.

This episode is 00:49:08 long.

This episode was published on Feb 3, 2026.

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