@Matt Motil  and its too small to be of any benefit if you need to sell you will not capture that. 

Were going to use the VA loan benefit that we have to purchase the property and live in one unit.

There will be many folks who can benefit from your experience, as well as those who are above you and can guide you in your future transactions. 

You may lose the benefits of property owned individually, like using building permits or representing yourself in court.See www.GeneralRealEstateAcademy.com for more info on TIC Agreements and fractional interests.

Their rational was that the only person benefiting from a further contribution were the beneficiaries of the IRA and that it should not create a prohibited transaction.

Also, has your Business degree benefited you as an investor?

Though I know he would be a major benefit for me, isn't this something I should have a good head on before jumping into?

Just for followers of this topic, This becomes your employee and has State Labor Board consequences, benefits, SSI and liability issues. 

My wife is a realtor so I have been able to hand off some to her to list on the MLS which is a nice benefit.  

I give the benefit of the doubt assuming they just don't know any better.