My brother and sister are entering college soon so I would like to help them buy properties to house hack!

That tort law says that if someone causes you to enter into a contract without both the intent and ability (money) to follow through to completion, they have committed fraud. 

I don't recommend you enter a contract to "hold" a property.

Add ~8% selling costs and if we enter a depreciation cycle the odds are small that the property will have positive cash flow.  

Its like when you deal with a tenant who has never been evicted vs. one that has - the one that has will know exactly how they can prolong and delay eventually getting kicked out and isn't afraid of the process.The estimating program they use is Xactimate which every PA uses as well, but the end result is only as accurate as the line items they enter - insurers frequently leave off a ton of stuff you'd assume is included but isn't.

The stairs to the 2nd floor go to the side of the house near the back entrance, so it would be really easy to add a wall so that when you enter through the back door you are in a small hallway that leads directly upstairs. 

Right now you are wanting to run in the Olympics and you have never entered a race.  

I'm looking for a Deal Analysis Calculator where with multiple Debt sources, I can enter a Private Lender Loan terms, and also the Seller Financing terms, for 1-5 y

We are now entering the counseling phase, however, we are keeping our options open and really looking to make the most out of our first home buying experience.

You also need to be careful that you are not entering into a prohibited transaction (which would be catastrophic).