Not huge cash flow, but it got me in the market and is a steady producer.

It sounds like you let things slide, which will result in an unscrupulous tenant acting more a fool.

Renting an SFH by the room can produce crazy good returns compared to traditional SFH rentals!

This would generally result in the distributed value being added to your taxable income and may incur penalties if you are not 59 1/2 or older. 

My goal is to gradually acquire properties that produce positive cash flow ($800+ monthly), so that I can become financially free.

“First look at the results where you’re currently living so you have some perspective.

There was a fire 3 years ago that resulted in a new roof, new electrical system, new siding as well as the house being jacked up a little bit while the floor was open.

Hello from a bp rookie that just listened to podcast #525 stop planning goals around results, do this instead w/ Geoff Woods. 

(a) If a condition results from an insured casualty loss, such as fire, smoke, hail, explosion, or a similar cause, the period for repair does not begin until the landlord receives the insurance proceeds.

The initial better cash flow markets are unlikely to produce the same long term return which is reflect in their better price to rent ratio.