Just depends on the situation/scenario.

You are bleeding money now, but each year it might actually get worse depending on the financials. 

I have a rolodex of connections if you would like.Also you can use a combination of the websites belowrentometer.comzillow.com  (look for the ones with a lot of applications

Everyone completes an application...don't you want to know who will be occupying your property? 

It all depends on what your requirement for cash flow is.

Depending on the valuation on the other property, you may be able to pull a HELOC on that one as well to get your $100k you're looking for.

The guy I signed up with basically knew nothing more than me filling out the application. 

The idea of debt-free is that if a person is going to retire and has to completely depend on the income, they don't want a severe recession surprising them and causing them to default on the debt and losing the properties.In a normal world, I would do that as well.

However, the entire market depends on Robins Air Force Base, with not much else moving the needle.

Whether to go with a BRRRR deal or multiple down payments depends on your risk tolerance and long-term strategy.