In the event of default/non-performance on a CFD for vacant land in one of the hypothetical "foreclosure" states I mention above, does the land parcel have to go to auction, with bidding starting at the unpaid principle balance of the contract (plus late fees, legal fees, etc.)?

You can normally work smarter not harder simply by investing in better real estate.The last thing I will add is the notion of cash flow and BRRRR being dual objectives.

@Zac Kucharek  I will focus on the asset protection component of your post since it appears to be the primary objective.  

I want to verify when calculating DTI, lenders will only look at the monthly principle and interest payments for each of the 5 mortgages and ignore the escrow portion (for taxes and insurance). 

It's not just about the numbers – it's about creating win-win scenarios where both parties can sleep well at night.3 principles I've learned after 4 years in real estate investing:1) Transparency builds trust. 

It was not a great personality fit, nor a good business relationship.Realtor #3: 4% sales fee - was very straight forward and objective.

I would argue that you can only save a finite amount of money when aggressively paying off the mortgage, but you have a much higher potential increase to your assets and wealth by taking that extra principle and reinvesting it into other investment instruments.

The last thing I’ll add is your objective even when you buy in C or lower class neighborhoods is to invest in neighborhoods that have the fundamentals that suggest they can transition to at minimum a B neighborhood.

A lot of OOS investors are falling for the shiny object in their cash flow spreadsheet, but it's not real.

What are your father’s financial objectives?