Hey Stephen,I looked into them but determined the "cost" of the money used made it prohibitive for me to do buy and hold.  

Plus, many of those addendum will have language prohibiting wholesaling. 

Hi Michael,Although I agree with Brian Eastman that co-investing with your IRA is less than optimal because of the increased risk that you might inadvertently commit a prohibited transaction, it is, nevertheless, possible to do so under certain limited conditions. 

In MN it wouldn't prohibit you from getting licensed but I don't know Illinois law.

To qualify for a solo 401k, you must be performing at minimum part-time self-employment and have no full-time W-2 employees.Following are the similarities and differences between the solo 401k and the self-directed IRA.The Self-Directed IRA and Solo 401k Similarities Both were created by congress for individuals to save for retirement;Both may be invested in alternative investments such as real estate, precious metals tax liens, promissory notes, private company shares, and stocks and mutual funds, to name a few;Both allow for Roth contributions;Both are subject to prohibited transaction rules;Both are subject to federal taxes at time of distribution;Both allow for checkbook control for placing alternative investments;Both may be invested in annuities;Both are protected from creditors;Both allow for nondeductible contributions;Both are prohibited from investing in assets listed under I.R.C. 408(m); andNeither may be invested in your own business. 

@Peter SchuylerThe following IRS web page is a good resource regarding what constitutes self-employment. https://www.irs.gov/businesses/small-businesses-self-employed/self-employed-individuals-tax-centerFollowing are the similarities and differences between the solo 401k and the self-directed IRA.The Self-Directed IRA and Solo 401k SimilaritiesBoth were created by congress for individuals to save for retirement;Both may be invested in alternative investments such as real estate, precious metals tax liens, promissory notes, private company shares, and stocks and mutual funds, to name a few;Both allow for Roth contributions;Both are subject to prohibited transaction rules;Both are subject to federal taxes at time of distribution;Both allow for checkbook control for placing alternative investments;Both may be invested in annuities;Both are protected from creditors;Both allow for nondeductible contributions;Both are prohibited from investing in assets listed under I.R.C. 408(m); andNeither may be invested in your own business. 

BUT... the only thing is that the guest house has its own separate water well electrically connected to the main house, and would be very cost prohibitive to have a 3rd meter installed on the property. 

If it did not jump out to me, some other readers may be missing key points, too.For example, the small dog/big dog I thought prohibited the big but actually allowed them both with a weird two category thing. 

It is a prohibited transaction.You may not think you are receiving benefit with your IRA investing however you are. 

Section 1701j-3(b)(3) says:In the exercise of its option under a due-on-sale clause, a lender is encouraged to permit an assumption of a real property loan at the existing contract rate or at a rate which is at or below the average between the contract and market rates, and nothing in this section shall be interpreted to prohibit any such assumption.That means would you lenders please go easy on the borrowers.