He seems like an intelligent guy, so the notion that a rent to own contract is too complicated for him and has too many moving parts is unfounded.

We have a few colleges around here, so it's definitely an option...however I remember the days when I was a student; my peers and I hadn't quite ironed out the notion of responsibility just yet.  

Most people go to the bank with a vague notion of what they make and have in the bank but all they can do is get an application and a financial statement form from the loan officer and go home and fill it out. 

I have adopted the notion that any thing worth doing isn't going to be easy and I am prepared to give it all I have.

It could also be a perceived notion that an FHA/VA will not close due to underwriting or that he cannot accept the slightly increased timeline.Right now it's just guessworks so pickup the phone and call the listing agent directly to find out the story. 

Right now, I'm leaning toward using the HELOC to put 20% down on each, and then roll an old 401k (that is worth 50% more than my stock) into a self directed IRA and use that to privately lend money.The notion of becoming a private investor is new to me--still reading on it, and looking for a good book/mentor to walk me through the process.

At least with that notion, you could take out a HELOC (if you buy right) and still have the best of both worlds.

There is the popular notion that one starts at SFH and moves up to apt & commercial.

@Mark Updegraff I respectfully disagree with the notion that anyone who's good at selling real estate has no interest in making "Peanuts" off of property management.

My current employment requires me to listen to peoples issues and than I provide feed back based on what I see, so my following opinions are merely insights, not necessarily advice.The following are based on 2 conflicting notions for you to consider:1) Learn from your mistakes.