If not, I looked up delayed financing on the Fannie Mae site.The original purchase transaction was an arms-length transaction.For this refinance transaction, the borrower(s) must meet Fannie Mae’s borrower eligibility requirements as described in B2-2-01, General Borrower Eligibility RequirementsThe borrower(s) may have initially purchased the property as one of the following:a natural person;an eligible inter vivos revocable trust, when the borrower is both the individual establishing the trust and the beneficiary of the trust;an eligible land trust when the borrower is the beneficiary of the land trust; oran LLC or partnership in which the borrower(s) have an individual or joint ownership of 100%.The original purchase transaction is documented by a settlement statement, which confirms that no mortgage financing was used to obtain the subject property.

If I'd have called my landlord a couple years earlier and found out he was interested in seller financing I could've saved a third of the price vs. waiting to ask about buying it 'til my self-employment and rental income made me able to obtain conventional financing.

Do I need to obtain a real estate license to do this or any form of certificate?

The Screen shot below is in your Fixed Asset Items List: This is where you can customize QuickBooks to show you everything you want to know about this property.

I like to hold appreciating assets and load up, buy as many as I can, and sell down prior to peak, when you see more supply/volume coming to market. 

I have had a few meetings with their leadership about cost seg and I know they have done reports for smaller assets like yours.Kyle

If you go your parent's route and you get a good W2 job, obtaining loans will be much easier. 

Brought 1st Rental property for $25,000 — Obtained financing based on a subject-to appraisal that came in at $50,000 @ 80% LTV = $40,000.My original thoughts were I would be able to only put $15K into the property and technIcally have none of my own money in the deal.

The transfer of the asset, with the sub-to note and pending tenant option deposit will also be somewhat complex and perhaps difficult under a custodian managed self-directed IRA.  

If you're even somewhat active in the purchasing/selling space, I highly recommend you obtain your Real Estate license for the following reasons:- CE credit often overlaps and counts toward both licenses.