Maybe determine a cash-on-cash figure that aligns with your comfort level.

Very much like the moon and stars need to be in perfect alignment, but it does happen from time to time. 

Cash FlowThis likely aligns most with long term or mid term rentals. 

Moreover, if your asking price doesn't align with the property's financials, it can stall the selling process.

Good communication will build trust and can lead to more investment down the line.When it comes to sharing how it worked for others, people often highlight the importance of alignment in investment goals and risk tolerance.

Ultimately, it depends on your specific needs and goals, but it's worth exploring to see if it aligns with your workflow!

It's a path that aligns with my skills and circumstances, but I could use some advice on how to get started effectively.If you were in my position, where would you begin?

I think the easiest way to find the right partner is to find one that you are aligned with as far as investing in rental properties.The other option would be to keep flipping properties until you get enough money for a down payment on a rental.Another option would be to look for a BRRRR (buy, rehab, rent, refi, repeat) because then your friend could still bring money to the table and you could pay them back their portion plus interest and then you keep the rental property.What area of Chicago did you do your flip in?

Once you have a plan, choose a market that aligns with your goals.

Financial Planning: How can a fiduciary help in aligning my financial plan with my investment goals?