I'd much rather have 5 properties purchased with debt that cashflow $200/month each vs 1 property owned free and clear that cashflows $600/month for example.

U need to buy this for 1.5 to max 2 to make any money if your going to bring on debt. 

Paying for their moving van and forgiving/discounting back rent due in order to get the lease terminated and the tenants out might be a much quicker/cheaper option.Just a thought. 

I have a couple credit unions I know of that lend 100% HELOC financing out on 1-4 unit owner-occupied properties so even if your cash is tied up in home equity you can draw from that line to purchase more properties as the tenants pay the debt down for you.

Most commercial notes are kept on the banks portfolio so they have a lot more room to work with so to speak as far as down payment, LTV, debt coverage, etc.

But I'm commission-only, and love the idea of creating a passive stream of income "just in case" and eventually paying off all debt and retiring at a ripe old age with $20,000/month of pure cash flow and 0 mortgages. 

Thank you for giving me a great starting point, questions to ask and tools to reference!

For example, if your parents bought 75% of the property and you bought the remaining 25% of the property you would need to put 25% of the down payment, be responsible for 25% of the debt, etc.  

Do mean his Total Debt is $400k?  

We have no student debt or outstanding loans except the rentals and our personal house.