HW are specifically tailored for owner-occupied properties and depend heavily on minimum expenditures/life extensions for failing home systems. 

I am a strong advocate of partially diversifying away from where you're heavily exposed.

Hi, Can some one recommend a book that focuses heavily on " evaluating a property " ? 

My main questions revolve around if the equity is taxed as a capital gains and if so, how heavily. 

Plus, I would I wonder if maintenance might be lower in a STR since often times people are not really using the property's facilities as heavily as someone who lived there full time would. i.e.

There is a group called the PII (Portland Investment Initiative) that are heavily invested in the area.

Much like Chris mentioned, Haverhill is investing heavily in their downtown area and has been growing steadily.  

Even if the purchase price is heavily discounted...

A lot of businesses are moving here to reap the tax benefits, and most of these businesses (especially tech companies in Austin) are HEAVILY targeting millennials with their work environment, benefits, etc.

I just did this on a house that was smoked in heavily for years.