The strategy may change, but every market can work.

I know this is a very old thread but if anyone comes across it I wanted to add some additional thoughts that might be helpful.

Buyers usually want to purchase on today’s value while sellers often want to use future potential of the property (“current rents are below market” or “room to build an additional property”, etc) to increase the purchase price or likelihood of a sale.

@Edgar Duarte Selling now under the primary residence exclusion avoids capital gains taxes, allowing you to reinvest the $500K equity in diversified assets like index funds or additional rental properties.

I would have contacted the locksmith tech to get additional details before assuming it was tenant damage.

In our market it is important to make sure they are a licensed broker, carry adequate GL and worker's comp (and name you as additional insured).  

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

And if you join Lowe's Pros, you'll get an additional discount (it's free to join).

and I also rent to voucher holders in the Milwaukee market. 

Given that you're not married, that adds some additional complexity.