All IRA-related transactions must be "arm's length", in other words, IRA can't get involved in any transaction with yourself, your immediate family members or any entities these individuals own or control. 

I love a good creative financing transaction when done safely and ethically.

Of course our big motivation is commission but you can get commission or a referral fee or something in an off market transaction if done properly.

We reimburse up to $15 per month third-party transaction fees for using the ATM cards, if incurred, for pulling cash out of an ATM machine. 

Keep this in mind before you jump into a real estate transaction prematurely.

They act as a fiduciary, and they charge a flat transaction fee regardless of investment amount.

You have to sell to realize your gains, and will lose on the transaction at this time.  

If you think about it, total engagement is $4000: if you back out an estimated $1,500 for tax based on Taxstra's quote, that leaves you with $2500/year or $208/mo for bookkeeping, which is a great deal (for reference, our absolute bare bones minimum is usually around $400/mo, and that's if you don't have a lot of transactional activity.)

Shane, buying "subject to" in Illinois is possible, but the state has stricter regulations around real estate transactions.

It has been mentioned above but your best bet is to separate the SFR and the 8 unit into two separate transactions.