We filed to have them evicted and the court issued a writ last December.

But 2-4 units is Chicago is extremely complex with 100+ year old buildings, Chicago zoning, department of buildings with violations and inspections, plus the RLTO. 

We spent four years in a duplex, maintaining it in our rental portfolio as we transitioned to another house hack residence with an additional accessory dwelling unit-type house next door.Navigating the intricacies of FHA loans in competitive real estate markets can be daunting, given stringent home requirements and more complex processes.

Options may include traditional mortgages, private lenders, partnerships, or even self-directed IRAs.Calculate all potential costs including property acquisition, renovations, property management fees, taxes, and maintenance.Property Selection and Due Diligence:Use your local team to scout properties that match your investment criteria.Conduct thorough due diligence including property inspections, financial analysis, and reviewing rent comparables (rental rates in the area).Make Offers and Negotiate:Submit offers based on your research and due diligence.Negotiate terms that are favorable to your investment goals, taking into account potential repairs or improvements needed.Close the Deal:Once your offer is accepted, work with your local team to complete all necessary paperwork and close the transaction.Ensure all legal aspects are handled properly, including title searches and property inspections.Manage Property Remotely:Hire a reputable property management company to handle day-to-day operations such as tenant screenings, rent collection, maintenance, and emergency repairs.Establish clear communication channels and expectations with your property manager.Monitor and Adjust:Regularly review your investment performance and financial metrics (cash flow, occupancy rates, expenses).Stay informed about market trends and adjust your strategy as needed to optimize returns or mitigate risks.Long-Term Strategy and Growth:Evaluate opportunities for portfolio expansion or diversification in the same or different markets.Continuously educate yourself on real estate investing best practices and market dynamics to make informed decisions.By following these steps diligently and leveraging local expertise, you can effectively navigate the complexities of out-of-state real estate investing and build a successful portfolio over time. 

Owners cannot get them out and have no support from the court system.

. - Types of assets with common seller carry potential include SFR's, Multi family (small balance) complexes, industrial or warehouse space, RV or Mobile home parks, storage facilities and vacant land. 

Purchase 1:  3 bedroom 3 bath condo in a *luxury* complex. 

I doubt this individual would want to go to court over anything.

Which will require a lawsuit and then the court to make the decision. 

you can't take them to court and ask for damages?