Also I realize this is a huge jump to make for a first time investor on a property valued so high, but I figured the terms were amazing and I am having a difficult time getting approved for conventional loans to start smaller.

Don’t make it more difficult than it has to be.

But a demolition order is very difficult to remove fi the city wants to be tough on derelict properties, even though they have a great ARV an d potential to help life the neighborhood.My Blog below has examples of how rehab loans can work or I'm happy to provide further details.

The mechanics of separating those interests isn't difficult. 

It's been difficult for me to put information together without context.

It is not that difficult.

Its not difficult, you just need to treat the deal as if you were buying it yourself.  

Short sales with seconds are always difficult unless the first can be paid in full and only the second is short.

Short-term rentals can be difficult to finance.

The OPs goal is to buy a househack which is going to be difficult if it needs a lot of repairs.As far as your strategy goes it could work but I think your expected response rate is high.