Applying that to RE investing, most would agree your first FHA loan should be a multi-unit house hack.

Can you move to a cheaper part of the country and house hack?

@Ken LatchersI agree about Airbnb.I get most of my bookings from VRBO/HA and I have heard alot of bad report in bookings.com so I'm not going to bother since I dont need them.

If you learn how to use Hard Money loans properly and how to find good deals in need of rehab, there are plenty of areas of the country where you could buy 3-4 rent properties in solid middle class areas with good cashflow.

He works with us often here in Chicago, but can service loans across the country!

Interest rates are pretty universal across country, you are in a high demand, high cost area.  

However, I'm assuming that my private investors won't agree to a POF unless they see the deal.Should I have a conversation with my private investors and ask how much they would be willing to lend?

Since you are out of the country and seem inexperienced, when buying condos you also have to assess the viability and strength of the HOA, pending litigation and/or assessments, and parking per unit.

With LLC Owner Match, DealMachine connects people to companies and companies to properties allowing you to find the owner or registered agent for nearly every corporate owned property in the country.

It is somewhat complex to try to explain on a forum, but at a high level, you (aka GP) and your family member (aka LP) would agree on how much the 2 of you would put in for the amount of equity needed (usually expressed as a %).