I'm an airline pilot and my wife a dental hygienist, looking for some passive income to supplement our regular income.

Medium term goal is to generate enough passive income to modestly supplement our incomes.

How are you going to supplement your current income during the transition.  

I want to learn how to take my "small" income and turn it into something I can be proud of by investing and supplementing it.  

A subsequent divorce, new child support payments, less time with my kids and having to rebuild my life sent me back on my original quest for passive income streams as well as re-establishing supplemental income from wholesaling with a new strong desire to complete my first rehab/flip but with an obviously significant need for private financing and/or hard money partners to help. 

If the latter, you would have to supplement all funds needed to make the purchase above the amount the lender is willing to lend against their value of the property.  

This is the coverage that would supplement any rents you would have lost after a covered loss that prevents your tenants from residing in the home and paying rent while repairs are being made.Water & Sewer Back Up coverage (it’s required by law in Maryland that this coverage is offered on primary homes/condos due to the high number of these types of claims in Baltimore city) is also included up to $5,000 which is really nice given that it is often coverage not made available on commercial rental dwelling policies.

It's not worth that extra 5-10k a year when you can pick up a rental to supplement it.

Perhaps you wish to supplement your retirement earnings for some future date.

Buy and hold requires more capital upfront and is more of a retirement or cash flow supplement for most people.