During this renovation period would you, as the lender, want an Actual Cash Value or Replacement Cost policy in place?

I’d look into the cost of a 500 sq. ft. garage and compare it to the potential boost in sale price.

This negative position can consume years of cash flow to recover.

This might give a one-time (non-scalable) boost to cash flow, offer multiple value-add options, and allow the house-hacker peace of mind, via the assumed mortgage, in long-term breakeven or positive cash flow in the event that the value-add plans end up not being executed, and/or the person has to move out, and rent by the room or STR become unavailable for some reason at a future date.

two families require way more cash and I don't have enough.

In 2019, I launched my own revenue management agency to help Airbnb owners boost their income and achieve greater returns on their short-term rental properties.

Understand how to "add value" to the property and evaluate cap rates, IRR, cash on cash returns. 

Stick to areas you know well; this familiarity can greatly reduce risk and boost your confidence when making purchasing decisions. 2.

Quote from @Shawn Questa: A few times I've reached out to Cash Buyers and they would tell me that they are a part of an Investment Group and that they are ready to quickly Close Deals would be happy to work with me.Later I would come to find out that they are actually a Group of Wholesalers, like me.I guess I would prefer to Work directly with the Investor, Cash Buyer or Flipper. 

We always check the assessor as we see people trying to boost unit count when it's not actually true.