Getting Started in rental property investments in Chicago

[Steven Antola]

I am looking for any insight with getting started in rental property investments. Based on my initial research, I believe that the "house hacking" method is my preferred choice. My 5yr plan is to acquire several 3 - 4 flat properties in the Chicago area. If I'm understanding the basic principles of that method, I would purchase under an FHA loan, live in it for one year, refinance to a conventional and purchase another under FHA live in that for 1yr, repeating the process until I achieve my investment goals. The long term vision is to build financial freedom, generational wealth, leverage the tax advantages of becoming a real estate investor and potentially cultivate it into my main source of income. I would appreciate any and all guidance.

[Travis Timmons]

You're in a good city for multi-family. The supply and commonality of 2-4 unit properties in Chicago is better than most cities. Familiarize yourself with owner occupied short term rental laws. I'd recommend medium term furnished rental (furnished finder, etc.) in the winter and short term renting from April to Oct-Nov. You take advantage of the cash flow from seasonal pops of airbnb occupancy and have a steady medium term (likely 13 weeks - standard contract length for travel nurses) premium rent in the off season.