Do you hold any financial advisor certifications?  

@Tina ArtigliereReach out to @Bernard Reisz (ReSure Financial) and/or @Dmitriy Fomichenko (Sense Financial)

Hi Robert, your situation sounds exactly like another gentleman I am working with right now and helping with his 1031 strategy and execution.

I am a 37 year old high school basketball coach that is not very happy with where I am financially and am seeking a way out of living paycheck to paycheck.

(I work with some challenging populations and the extra effort has paid off in these situations.) 

As you might already know, house prices in New York are extremely high, which makes it financially difficult for me to try house hacking here at the moment.

In high-cost markets like Chicago, that can be tough to meet.If you're looking at a duplex, the self-sufficiency test doesn’t apply, so you’d just need to qualify based on your personal income and the rental income your lender allows.If your current lender isn’t familiar with making FHA work in your situation, it might be worth getting a second opinion from someone experienced with FHA multi-unit financing.

In the past year we've been through the ringer financially due to bad contractors, deal promises, and generally just being new to the game.

You can verify us through the following link: https://nmlsconsumeraccess.org...Our Lender License is issued by the California Department of Financial Protection and Innovation.

Perhaps check with a local attorney before proceeding.I realise I left some stuff out in the beginning, but the whole situation in general is just pretty wild.