HML - You have a challenge here:  If you are looking for hard money to purchase with the goal of refinancing, you will (frequently) need to show that you can refinance. 

I think @Corby Goade said it best with regards to the challenges with purchasing a condo unit as an investment.Most condos in NY require 20% down...

I agree with @Justin Abdilla's approach as these situations can be emotionally driven and may become legally challenging.

This will be your biggest challenge.

My blindness requires that I establish alternative systems to identifying sellers and buyers, and successfully closing deals, a challenge I am ready to crush.Below are some of my goals with wholesaling.To build cash reserves.

Changing tax paying entity prior to a sale and commencement of a 1031 has consistently been challenged by the IRS. 

I agree "emotional" is challenging.

Before engaging with Airbnb rentals get legal advice and do your research.

the challenge of course is going to be to find the right replacements and fit into the identification calendar as well as the potential nightmare for funding approval given the moving pieces.If that proves daunting you could also think about buying one or two properties for cash and then refinancing them immediately after the 1031 to access the money for the next two.And yet another option that a lot of our clients are choosing these days is to separate the cash and debt as a form of defensive investing. 

The challenges with subject to deals come up with the due on sale clause and the insurance.