It has a Walmart, Lowe’s, Home Depot, Applebees, and a 99 Restaurant which is a New England chain as well as tons of other businesses and restaurants.

.- Material participation rules still apply: If you meet the IRS material participation tests, losses from a short-term rental can be treated as nonpassive, allowing them to offset W-2 or business income.

The institutional firms that do this type of lending (we deal with them every day) have to "securitize" the loans...meaning have their hedge fund/Wall Street backer bless the deal.

Also, when evaluating a value-add deal, what are the key factors you prioritize most? 

You’d need a full year of business tax returns (not a partial year) and ideally a prior W-2 in a similar field with comparable income.

Quote from @Don Bessette: First, you need to realize this is a business relationship.

Are the days in the contract calendar days or business days,?  

This is really going to depend on the state you are looking to do business in.

However, if you’re a real estate broker or active trade or business, then you may be subject to SE tax depending on entity structure (just like a normal business).

You have to come to the table (a future deal) with funds to get the ball rolling.