@Alec Barnes we use Debt-To-Income Ratio (DTI) instead of income = 3x rent.Reason?

any lender wants to know how you plan to service the debt.

So, if you put in 20K, you could set the bid up to the amount of the 100K total debt(80K existing + 20K additional) to ensure that the property reverts to you as the lender.

How much weight do you give to the cash flow benefit of cheap debt when the property is priced above market?

Eliminate debt, establish a budget, and save.

I also use their virtual credit cards which enables me to assign a card to a specific person, like the cleaner for my STR for example, so when she runs a charge, it automatically drops into the right account in terms of categorizing my expenses.

Even if a title company were to manage the setup making sure all parties are paid, the cheap debt and cash flow would not be enough to be enticing to any investor even if midterm rental could yield a healthy return. 

You may just stumble into seller financing if play your cards right.

I calculate the returns on the entire investment, since your debt applies to the entire investment.

I am looking for any recommendations on how to properly scale this idea over the first few years conservatively and not wanting to over use leverage and debt by starting small in duplex and being open to triple/quadplex in the future if the right opportunity presents itself.