Hello all. Member of my family are cashing out on an industrial real estate investment that they held more than a decade. We will be under contract as of this week. In order to defer some of the capital gains, we are looking to reinvest in rental properties. We own several other 2-4 units in the city, and as for myself I have flipped a couple of different single family homes in the city, I also used to sell homes for an investor/flipper (without an R.E License). We are not new to the game, but the undertaking we are considering is definitely out of or real of experience, maybe even our comfort zone. Regardless, we are looking to move on this and I am in the beginning stages of mapping this monster out. What are we getting ourselves into? I am already looking into property taxes, Property management and Cap rate comparisons. Any advice and direction would be greatly appreciated.

Here are the two properties we are looking at.

https://www.loopnet.com/Listing/7329-N-Honore-St-Chicago-IL/21891991/


https://www.loopnet.com/Listing/5317-N-Hoyne-Ave-Chicago-IL/21935181/