Quote from @Steve Englehart: I currently have two long term rentals and am looking into buying into the short term rental arena.  

Paulette, it is good to call out these bad contractors and unfortunately you are caught in a bad situation on what to do, start by a small threat that you will contact the BBB and report a claim if he does not show some progress, or if you know an attorney, maybe a simple letter from one may get him worried and he may start showing up.

I probably won't withdraw it, so the long-term tax savings and asset protections are appealing.Anything I am misunderstanding or not considering?

Not overpaying and getting great terms 3. multiple bids/ quotes 4. project management. 

I’ve been in the industry for several years, and my work has given me a solid understanding of property systems, maintenance, and what makes a home a great investment.I’m now looking to expand my own real estate journey by learning how to acquire and manage short-term and long-term rental properties.

After years of focusing on my career and building financial stability, I’m ready to dive into real estate investing and start creating passive income and long-term wealth.My short-term goal is to purchase my first duplex or single family rental. 

Maintenance and potential repairs will also require a long-term financial plan and setting aside a contingency fund for such expenses.The steady cash flow, appreciation over time, and tax benefits can make a meaningful difference to your wealth in the long term, especially with the principal paydown on the mortgage.However, if managing the property from a distance feels too burdensome, or if you’d prefer the certainty and flexibility that comes with having less debt (especially given the high mortgage rates), selling and using the $100,000 in equity to reduce your loan for your next home may be the smarter move.

Really depends on what they are looking for as well as long term plans.

Do you think you will be in TN long term?

Owning a duplex at 20 is a huge accomplishment, and it’s inspiring to see you’re already planning your next move.From my perspective, real estate investing is a long-term game focused on building equity, paying down debt, and maintaining stability over chasing short-term cash flow.