Flipping is high risk and can go wrong if you don't know what you're doing (or overdo the renos).For your house, run the numbers to see what it would look like as a rent as well as your own home. 

I have been doing TurboTax for last 20 years and some of my real estate i purchased were in 2009(condo) and 2013(townhome) timeframeSince you purchased your properties in 2009, you likely purchased the properties at a lower price point than what the houses would sell for now.This means that your depreciation would be lower than others who purchase homes now.You should still have a benefit by depreciating the homes.

We are headed out to Bremerton this weekend to see the house we are purchasing in person.

@Troy Zapp, if the wife is on board, start exploring the investment strategy of house hacking to minimize monthly expenses and watch your income snowball.

I also thought about buying two houses in the same deal, but my long term broker (the 30% broker) who said they can not do that. 

Purchase price: $234,900 Cash invested: $7,000 I house hack 2 bedrooms in a 4-bedroom home as Mid-Term Rentals.

A lot of the STR management companies have contracts with companies to house their employees when they travel for extended periods of time.

Financially speaking house hacking with a duplex in Milwaukee is a no-brainer.

Even "turn key" rent ready houses will have some expenses.

I sold the house for $180,000 and made a decent profit