@Nathan Richmond if you have employer retirement plans you may be able to take a loan.

If you have a private loan, you've already taken care of the biggest obstacle, which is getting approved for a loan with the inconsistencies in your self-employment income.The key here is to find a property where the other side of the duplex (or multiple units, if you find a multi-plex) are paying as much of your monthly mortgage payment as possible.  

A Basic list would look like this:- 2 Years of Tax returns - 2-4 Pay Stubs - Proof of current employment - An Idea of your Credit score- Length of time with current employer - 2-6 months of bank statementsThis is not an all inclusive list but will give them a good idea of where you stand.  

I'm under the impression that you cannot invest your 401k with your current employer into real estate, and you cannot roll it over into an IRA until your employment ends.Old 401k's can be rolled over into a SDIRA.As far as the OP is concerned, most 401k plans offer a fund that matches the S&P500 index.

If you have verified the employment with the school they should be fine.

Every bank we have talked to has said the same thing, they need two years of tax returns from 1099 employment before they will even look at giving you a loan.

I would just mention to him that what you witnessed isn't ok,  but he's a good contractor and you would like him employed but there's lines that can't be crossed.

The company was a subsidiary of her current employer and when I asked about the property, she knew the address but informed me that the loan was in default and sold... also about 20 years ago! 

I know he is protecting his employer, but I feel like I'm swimming in a shark tank.

@Ha Dang Some good advice above, also consider that generally any loans borrowed from a 401k are due for full repayment if when you are no longer employed by the company, in the event you voluntarily leave or are let go (knock on wood).