I have a background in design and hospitality so I pair that with my knowledge on the real estate side of things.

Then, the program is designed to help people get back on their feet not subsides their rent forever like other programs.

https://www.biggerpockets.com/airbnb-calculatorI would not go cheap on the furniture and really pay attention to the design and amenities you can have that compete with the top places near by.

Spent majority of my adult life (2 decades) working with adolescents on Young Life staff.

(Noticed I didn't include architects in that list - from my experience most architects are great at building design but shouldn't try to do land planning.)If you have never done any development like this before than it would make sense to partner with someone who has (or flip it entirely) once you have a site plan of the property's potential.

I rented out a 3 bedroom,  2 bath house to a family with two adults and two children. 

Short sales by design are listed on MLS (always and always are arms length) and not below value, or the lender would more than likely decline any short sale offer.

If not, hire a professional architect or floor plan designer, or use tools like RoomSketcher, MagicPlan, or Matterport to create them.

You're correct to say that industry is high inefficient, that's because it was designed that way.

It can be a conversation in search of a win-win, a mutual effort vs adversarial negotiation as on-market is designed to be.