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My fiance and I are currently exploring house hacking opportunities in Chicago.

I would get my side hustles going, get my spending down as low as possible, get my credit score as high as I could, and try to get some real experience by working with/getting to know experienced guys in the market/business type that I am interested in exploring.

I have been exploring Realeflow for the past few weeks and it seems to be very sound as a lead finding tool.

Currently working with American Heritage Properties but I'm interested in exploring other possibilities as well. 

So I have been exploring different ideas and options to moving forward, this idea being one of them.

Are there any other options I could explore or do I just need to raise more money for my first deal?

Expertise rather than locality will be a key factor you wish to evaluate when exploring the field. 

Assuming that’s not in a high cost area, house-hacking while working and knocking out your associates might be another route worth exploring.This would give you an opportunity to explore both college and REI before doubling down on one or the other.If you can suffer the cold, Cornell has a great real estate program, is transfer student friendly, and offers solid financial aid.

A few things that may be helpful to you here on the Bigger Pockets website as you search for a team to support your first buy:You can set up keyword alerts so anytime someone posts about Charlotte (or the specific neighborhoods you're exploring), you'll be notified.