Park Hill has always been sought after, but this will only increase it’s desirability…..

It hedges any downside risk and increases cash flow.

Courtesy of Dodd Frank, its doubtful the self employed will ever be viewed by lenders as favorable as a w2 employee.

A self-directed IRA or 401k can be a great vehicle for loaning money to others without getting hit with taxes on the interest income.

Quote from @Jonathan Blanco: Is it worth seeking lenders with $0 lender fees (such as origination, processing and underwriting fees) or do they just get that money by increasing rates and charging higher points?

Gradually introducing her to the benefits and starting with a manageable investment can build confidence and mutual understanding.This post does not create a CPA-Client relationship.

Whichever direction you go, be sure to work with folks who understand this and gives you the confidence to take reasonable action - I'd personally take an okay investment and weather the storm for a few years that will eventually perform well, and do that each year - rather than take 3 years to wait for the best deal possible.

This is where you can significantly increase the value of the property by making improvements that attract quality tenants and justify a higher rental price.

But if you can finance a home in an appreciating area make it breakeven and at some point (as always) either rents/nightly rates will increase, interest rates will go down, or both. 

I have one rental property that I have been self managing for about 10 years but I'm looking to exploring and potentially doing my first Flip this year.