Hey derek hope u make out on the 1031, hypothetically if you could break even if it were a long term rental would you hold it? Thats the situation im in Semper paratus!
You are making the right decision of letting it go. Not only because you are up on it but you ran it through the mental equation which is so often overlooked when making a decision as such. The mental aspect of not having to deal with the property probably returns way more than the monetary gain from the sale. Also, you are no mug with your money so I'm sure you will move the funds from the sale to something else that requires less mental energy and probably gives even better returns in the long run.
Great perspective and insight, thank you for sharing. Personally if it were me I would sell, take the tax hit and invest the proceeds in the stock market (I’d go a combination of the “magnificent seven” and an S&P 500 index fund). No stress, watch your money grow
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If you are at least close to break-even after paying mortgage, HOA, and professional AIRBNB host then the smart thing to do is to hold. Being a real estate professional/entrepreneur, the tax hacks/advantages are enormous. You also mentioned that this location outperforms the Hawaii market. As a real estate investor, the main thing is looking at it as a long term play. Imagine yourself 10-15 years from now with its possible appreciation by then. Would you say, "I'm glad I let that go in 2024" or would you say, "Gosh, I should've kept that place, I would've own it free and clear by now." Personally, looking back at a couple of the properties I owned and sold, I now wish I would've kept them all. Those would've been paid off and 100% cash flow with its equities I can leverage from. Just food for thought.
