It sounds like you are working through this in a wonderfully systematic way -- great work!

It's a good approach.

House-hacking is a great way to get started, there' s a huge market for those looking to rent individual rooms in Denver, have you considered that approach?

How did you approach the seller about the credit deal?

Of course it all depends on your strategy and business plan, just something to think about as you look at areas like Carmel where the average home price is approaching $400,000.I have heard good things about the Brownsburg school district but don't have any personal experience there.

There are pros and cons to both approaches, so think about what you want.If you are buying in the city where your mom lives, find a good realtor that works with investors and go there for a weekend to look at properties.

To address your S-Corp tax election on an LLC this is specific to the client situation hence entity structuring is never a one size fits all approach. 

Over two weeks ago, he approaches me with an idea for some '2nd chance' program that could allow her to buy another house and pay less per month than rent. 

Without getting too in the weeds, here's how I would lay out an approach to finding a good syndication partner (I visualize this like a funnel where the numbers get reduced at each step):1.

Does anyone have any advice on how I can approach this to give them a second offer?