top of page
Search


My Failed Vacation Rental Cabin Sale: What Really Happened and What I Learned
I ended up taking wild ride with the potential sale of my vacation rental cabin in Tennessee, so I figure I owe you guys an update. When I last wrote about it back in October, we were debating whether to accept a lowball offer after having the cabin on the market for the past 9 months...
Dec 11, 2025


Should You Sell a Rental Property at a Loss? My Real-Life Dilemma in the Smoky Mountains
After months on the market, I finally got an offer on our Smoky Mountains vacation rental — but selling would mean a $150K loss. Do I sell now or hold and hope the market rebounds? Here’s how I’m weighing the decision between cash flow, taxes, peace of mind, and long-term strategy.
Oct 16, 2025


Depreciation Recapture: Paying Taxes on a Loss 😬
Learn about depreciation recapture and how it can apply even if selling at a loss.
Sep 25, 2024


My Money-pit Beach Condo: A Post Mortem ☠️
I thought it would be interesting to do a post-mortem on our beach condo investment to show what went wrong and share some lessons learned.
Sep 11, 2024
bottom of page
