When doing a cash out refinance, it's important to consider seasoning periods of the waiting period you have to have between when the old transaction closed on the hard money loan to the new cash out transaction closing.

If it is a credit/equity line, you could provide a lender letter that the funds are available immediately for funding - and cured any recission period. 

Were they all completed within the same 12-month period, or did it take longer?

It's no guarantee but it's a good place to start.

During this 24-month period, the property must be rented to another person at a fair market rental value.After the 24 month period your sibling could convert it into a primary residence.

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

Even with guaranteed rent, it's important to thoroughly vet applicants.

If this isn't required, then most likely having the GC sign a completion guarantee to ensure the project gets finished and lender is not stuck with a partially complete asset is the case. 

I guarantee most will point to someone else for the overage.  

Even better, I might be able to snag it well under market value since it's an estate sale that's been sitting on the market for nearly 200 days.Here’s the challenge: while I could afford to purchase the property under market value, I’d be stretching my budget thin to cover the mortgage during the period I’d be remodeling the basement to make it rentable.