In my case, I have residential rentals in one LLC, commercial properties in another, self-storage in a third, and my real estate company operates in a fourth.

If you pay two years' worth of property taxes in 2025 (January and December), both payments are deductible on your 2025 return, potentially reducing your taxable rental income significantly.

Regardless of how you financed your rental property, you can generally deduct repairs and take advantage of depreciation schedules.

However, the market is competitive, and rental regulations are becoming stricter.

.✅ Hands-On Experience – If you plan to grow your real estate portfolio, managing tenants yourself can teach you valuable lessons about leases, maintenance, and local rental laws.✅ More Control – You’ll personally handle tenant screening, rent collection, and property upkeep, ensuring everything is done to your standards.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

Austin area seems like a cool techie area with good rental demand.  

Hey friends, I'm an agent in Daytona Beach and I locking in my first short term rental listing.

Focus on long-term rentals in affordable markets with reliable cash flow, and steer clear of high-cost flips, lower-class properties, or overleveraging in areas that rely solely on appreciation.Good luck!

Congrats on your success so far.Some random thoughts for you:- It might be difficult to tap the equity in the rental at this time given the current state of interest rates.