It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.

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The cash on cash return is only meaningful when you evaluate it based on your long term plans.

I plan on using that equity to get myself into real estate investing.

For the BRRRR process I plan on using a hard money lender for the rehab process for the SFH's but what I'm not sure of is, should I purchase a duplex and rent one unit out and live in the other or should I just rent for now, not purchase a duplex and just purchase a SFH with cash and start BRRRR'n immediately?

ESP if you are planning to lowball, an agent might be more reasonable to discuss with (seller might get emotional and offended with your offer).

It depends how long you plan on living.

We plan to share ownership of the property as I am going to invest my money into developing (building a Detached ADU in the back) and re-modeling the property so that we can collectively sell it for a profit.

I currently have my investment portfolio all in North Jersey and planning on purchasing a number of units in Syracuse.

I know that is a long pay back period but don't plan on selling anytime soon, plus you never know what nat gas prices will do.