You did an excellent job summarizing your experience. I enjoyed reading about your first year of investing—it’s clear how much you’ve learned. Managing tenants yourself is no small task, but I’d say it’s often a blessing in disguise. The challenges in real estate teach you invaluable lessons that you might not gain otherwise.
I also invest in Chicago, so I have a few thoughts in response to the questions you raised. Regarding evictions, it depends on the time and resources you have available. I know a friend who is an attorney, although they don’t specialize in housing law. Even so, they were able to help at times when I had technical questions about the legal process. I’ve had two evictions in the past two years. Like most, I was evicting tenants that I incurred through property purchases. I have been fortunate enough to be successful in both my cases and just getting to the point right before going to a jury. Nonetheless, If you’re short on time, hiring a local attorney who focuses on evictions is definitely a good idea, as the process can be quite tedious. From what I’ve heard, it costs around $1,000 to initiate an eviction with an attorney. However, even issuing a five-day notice can be an important step before filing. Spending $1,000 to start the process can be worthwhile if you’re clear on the steps needed to reach that point.
As for renovations, the approach really depends on your goals and the scale of the work. I’ve learned through experience that if a renovation will take several weeks or months to complete, it’s usually better to hire contractors. Time is money, and delaying a renovation often means lost rental income. For this reason, I prefer to plan renovations when a long-term tenant moves out. For example, I have a tenant who has been smoking in their unit since before I took ownership of the property. When they eventually move out, I plan to do a full renovation to bring the unit up to high-quality standards and maximize its rental potential.
I’m happy to connect if you ever want to chat.