I would go ahead and have a contract drafted up despite this being a familial transaction.

EVERYONE involved in the transaction just got screwed.

The individual purchase prices were adjusted so the IRA was making a "bad" investment, but a good chuck of the IRA funds were able to be pulled out through the transaction for use and multiplication today.  

Transactions are everywhere.

Can she facilitate this transaction under herself or any entity because she’s the sole owner and taxpayer?

While you are the trustee, everything you do should be an arms length transaction that should be benefiting solely the trust and not benefit you.

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If this is your first investment I would not recommend going through a wholesaler or an off market because like @Lucia Rushton mentioned you will not be properly represented in your transaction. 

I cross check that against what my realtor and other local folks I have relationships with tell me about where the neighborhood is trending, as well as rent-o-meter and searching for high-level rental data/trends.

Is it possible to wholesale with a short sale WITHOUT double closing or using transactional funding?