Like tech start-ups (the world I know), anyone can put together a nice presentation, but credibility is the key to reducing risk. 

That said, if the private investor is experienced and simply providing financing,  s/he would have presented you with a set of terms (rate, duration, costs, etc).  

When you have a deal that you only think is a good deal, it will get turned down (no one ever presents a deal that they think is a bad deal).Good luck.

(I’m one of the presenters.)  

I’ll defer the interpersonal relation question to someone else :)

Yes, this does present the challenge of both individuals needing to be able to qualify for a loan on their own, but it’s a great way to do it.

@April Oswalt if you have something I have buyers that I work with that I would be happy to present the deals to.

Hailing from good ol' New Jersey, I am new to the world of real-estate investing and I felt the timing couldn't be better to kick-start this journey (new decade -new hopes and aspirations) Presently, my goal is to build a portfolio of MFH's over the course of the next 10 years.

While it may cashflow now, my concerns would be higher maintenance costs and tenant quality/stability issues that stem from the overall functional obsolescence that's present in a lot of Chicago's 100+ year old housing stock.

I’m reading that the capital gains invested are only deferred until 2026.