However, the tax treatment differs between short-term and long-term rentals:Short-Term Rentals (STRs): If you materially participate (work 100+ hours and more than anyone else on the property), you may be able to offset rental deductions against W-2 or other active income, offering greater tax benefits.Long-Term Rentals (LTRs): If your AGI exceeds $100K, your rental losses may be limited, unless you qualify as a Real Estate Professional (REPS).If you plan to expand your rental portfolio, consider an LLC later for liability protection and easier management.

One is under contract in which I plan to 1031 into something larger and the other I just plan to keep as the contract expires soon.

We closed on our first property on November 15 and plan to employ the fix-and-flip strategy. 

Plan is to purchase a couple homes over the next year.

If you're wanting to get into construction managment there's two main areas you would need to make yourself an expert in; Reading plans & Scheduling.

Make sure your wife agrees with this plan, though.

All are local to me in a non-vacation rental spot.

People will always vacation.  

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.

Unfortunately, relying on a "nice card" approach doesn't always ensure that tenants will vacate the property in good condition.