Was built in early 60s and if I had to categorize the style would say poorly executed art-deco. 

Kerrville is known for art and wealthy retirees.

The quality of life is second to none, the amenities of Greater Portland are fantastic (food, art, recreation, entertainment, etc.) and population is growing. 

If #1 & #2 are the "math" of the deal, #3 is more of the "art" because it's based on experience and gut feel developed over the 2 decades of doing this.

I would love to see this property rehabbed and leased out as office space, or even build a relationship with the local university as their Fine Arts building is right next door to this property.

It's more art than science, but here are some considerations:Landlording Climate - I'm a buy-and-holder, so I'm looking for markets that are landlord-friendly.

Then you add the art to the science and consider things like your job stability, property locations/demand, commission/salary, children/spouse or not...plus just your ability to sleep at night and add those to the equation.Good question and a good exercise to monitor your personal balance sheet regularly.  

This is where some art more than science can come into play.

Except Reagan, I've heard lots of things about it and the performing arts school as well. 

I like Temple as an investment....the University has been investing in their own area, plus they expanded their medical school and the center city area has been in developing in that direction, plus Avenue of the Arts is seeing some incredible growth.