Where should I invest next?

[Ryan Peach]

My goal is to "retire" in 5 years. I want/need roughly $8,000/month to cover my current income and benefits. I live in Evansville, which is growing but still a small/mid market. It is currently saturated with investors and housing prices are crazy high for the area. I live 2 1/2 hours from all of the following: St. Louis, Nashville, Indianapolis, and Louisville. I'm afraid if I wait for the market to settle here I won't be able to reach my goals. If you were me where would you try to invest next? I have 2 local rentals now, have flipped in the past, and like the idea of Airbnb.

[Andrew Johnson]

Ryan Peach So it's wonderful that you have a goal but so far there's no data about how close/far you are from that. Are you carrying debt on the two rentals? Are they generating $100 per month each in cash-flow or $1,000? You'll never reach $8,000 per month trying to get 10 SFRs with conventional financing (30 year fixed) if they are cash-flowing $100/month each. Do you have zero dollars in capital today or $500K sitting in the bank? Do you want to self-manage when you retire? If so, Evansville (local) has economic value to you. Even more so if you ever contemplate short-term rentals where property management fees (percentages) are decidedly higher.

So if I'm in your shoes I'd lay out what your projections are to get you to $8,000 per month. How did you pick 5 years? Is it an arbitrary "want" or does your spreadsheet tell you its achievable in 5 years? What are the analytical assertions assumptions that yield an achievable result?