In short, these are great supplement tools to make screening or receiving payment more convenient, but they are not substitutes for developed intuition and property management.

@Devin Redmond Do you feel the goal of Stessa is to replace Quickbooks (or other software) or just supplement them? 

Supplemental rental income?

If your goal is to have 1 or 2 rentals as supplemental income as you age, then I agree paying off all debt sounds great. 

Why is that I can buy a SFH at 640k no problem, but I cant buy a triplex even though I have been approved to make the mortgage payment without even considering the supplemental rent if I had to? 

Are you looking to bring in cash flow to supplement/replace income?

We would have to supplement the rent for a few years, but these properties are million dollar homes with great value.

Then, rinse and repeat.When designed and implemented properly, you should be able to purchase multiple properties over the years, and still have a way to supplement your retirement in the end with the cash value.Feel free to reach out with any follow up questions.

Use the money you will be making within the oil field and put it towards building a real estate portfolio with sold cash flow that you can use as supplemental income once the oil field turns and money is harder to come by again.

If cash flow would go negative following a refinance then it will be up to you to decide whether or not you want to keep the property and accept a negative cash that you will need to supplement in the short term because your goal is long term appreciation in the area or whether you would rather regain your capital and take the immediate profits in order to put into another property.