OOS just complicates things for most people. 

If he doesn’t file for bankruptcy and holds on for a little while longer while getting the 1st short sale and then is forced into bankruptcy anyway, it is conceivable the trustee will seek a "claw back" on preferential payments complicating both his and his previous lender's life.

I would just really stress the complications associated with transferring title post-close with a conventional mortgage.

You don't need a license to wholesale, and it can make it more complicated if you do have a license. 

I've seen a lot of conflicting advice that cautions to avoid areas with high crime rates due to complications and extra costs from the tenant base and property crime.I understand that both cities have shown crime rate improvements, but their overall rates are still way above average.What makes these cities attractive for investment despite this?

Buyers get spooked easily, plus every year the process gets more complicated with financing, appraisal and inspection issues (which can vary from lender to lender) that could be easily overcome threatening to crash deals without someone experienced in there herding all the "cats" (lol- elements) in the deal to a successful close of escrow.Also most of those comps you are seeing-maybe even all of them- have had a commission and some fees paid by the seller, and the appraisors are aware of that.I hope your home sale goes smoothly.

The transaction was a little complicated because the buyer was a group formed by an investor owning a 40% interest in the subject property (my partner and I were the managing partners of the current owner entity and 60% owners.

From air rights to zoning laws, it can get complicated but I believe with the right team of people, it’s possible to create opportunities where others didn’t see or gave up soon.  

I was thinking maybe we could set up a ACH auto withdrawal from her bank or unemployment card to ensure the rent, any thoughts or complications with that? 

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.