Part of the issue depends on what market your buyers are from and where they live..

Live in one unit and rent out the others to cover your mortgage.Seller Financing: Negotiate terms with the property seller where they act as the lender, often requiring a smaller down payment and bypassing traditional underwriting.Partnerships or Joint Ventures: Partner with an investor who provides the capital in exchange for a share of the property’s equity or income.Lease Options: Use a rent-to-own agreement, which allows you to control the property while saving for a formal purchase.BRRRR Method (Buy, Rehab, Rent, Refinance, Repeat): Acquire a distressed property with short-term financing, rehab it to increase value, rent it out, and refinance to recoup your initial investment.Pro TipStay in close communication with your lender as you approach your next purchase.

Is the buyer going to have the same issues with the property that you’re having?

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

The house has some "hard" issues: 1. pretty steep hill in the front with stairs to the front of the house.

I am not sure that I understand the title company's issue, as you are probably personally the Manager of the managing LLC.

Yep I look at it this scenario like issuing a hard money loan to myself since I recoup the interest in the 401k.

I would keep and organize all of your communication around this issue, including gathering pictures of the unit and the area in question that was repaired.

Sewer issues in Chicago are very common which is why I ALWAYS recommend / almost require my clients to get them done + if there's trees in front or in the back of a property, there will almost always be plumbing issues + needed rodding. 

Furnished Finder does make it tricky since you need separate profiles for each room, but platforms like Apartments.com or Airbnb might work better if you're aiming for full-house rentals or structured by-the-room arrangements.If you decide to rent to multiple individuals:Tenant Screening: Screen each tenant thoroughly to ensure they’re reliable and responsible.Clear Communication: Introduce potential tenants to one another Detailed Agreements: Use separate leases for each tenant and specify shared vs. private spaces, utilities, and maintenance responsibilities.House Rules: Create clear, written house rules to prevent misunderstandings.Inventory Tracking: Document everything in the home (furniture, appliances, etc.) to avoid disputes about damage or missing items.Also, market your property with its flexibility in mind—like proximity to hospitals for traveling nurses or universities for graduate students.