Quote from @Ashish Acharya: @Niklas Zhu If you tear down your STR in 2025 and convert it to personal use, depreciation recapture does not occur at the time of conversion.

It will also allow you to focus more of your time and resources in the actual real estate vs. raising capital which usually leads to poor real estate acquisition and operational decisions because raising capital is your full time job leaving an inadequate amount of time for the real estate.OK, chasing 32unit apartments, acquisition priced between 3.2M - 4.8M.  

.✅ 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.

Have you taken the time to search AirBNB and VRBO in those specific areas to see how many STRs are operating?

For more affordable properties—those priced under $400,000—the timeline is even shorter, with many homes receiving offers within two weeks of being listed.This fast-moving market poses a particular challenge for first-time buyers who may not be as familiar with the urgency required in competitive bidding situations.

Spending a healthy % for a reliable company can make your life easier and lead to more growth as you free up your time.

As a newbie, you always question whether you're making the right decision, but you just have to push forward after a certain amount of time to prevent analysis paralysis.

How many times can you spend $1500 to get an 88% return?

Any guidance would be most appreciated, so we can be better prepared for our tax returns next year.Thanks so much for your time !

If you have an adjustable rate mortgage and it is likely to increase significantly in the future, rent growth rate may not compensate for this and cash flow is likely to get worse over time.