I'm planning to invest, start small and get my way up which area you think is the best for me to start looking?

Sell the home- I would keep the home vacant and wait until spring season to sell.

By the time Spring comes around, they are used to the new rent.I have low turnover in part because my rents lag the market.

To stay ahead of any issues, we offer coordination of gutter cleaning and furnace tune-up every fall and spring clean-up every spring. 4) Own the outcome—This is the philosophy we live by.

So at the end of the 5 years, you are just treading water with the lower price point home, while you made headway with the other one. 

I love the idea of fix & flip right now @Abigail King, especially right now here in Chicago and I am sure it is similar for you in central Illinois -- it's winter so there are way less buyers and if you can get under contract soon you can likely rehab over the winter months and hit the spring market!   

Our occupancy rate has been higher this fall, using Airbnb and VRBO than it was during the summer and spring months, when we were listed on all 3 platforms.

If I buy a house for $400k, and the market drops and the house is now worth $300k, I am under water.

In late spring through summer season i am virtually 100% booked.  

The agreement stipulates:"The owners agree, that no water shall be used for commercial purpose, but only for their private domestic use including vegetable gardens and livestock maintenance."