For example, lets assume the house is worth $100k now.

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'm in Phoenix, where it's brutally hot in summer and a lot of houses have pools. 

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

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.

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. 

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

This assumes the market rent for the unit I will be moving into.My goals from entering real estate are 1. add diversification in my investments (right now heavily invested in stocks) and 2. house hack, so that tenants pay part of the mortgageIn my current market, I have two options: a. buy older houses, renovate, bring the rent to market --> this will cashflow, but needs a lot of time investment which I don't haveb. buy turnkey properties: --> renovated and already occupied by tenants but may not be cash flow positive.I found a property that's type B.

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