As a homeowner turned renter and retiree from another state, I had assets (savings account balance) to prove my capacity to pay the rent for a year and a good credit score to prove my character of paying my bills on time.

@Thom SouleLOL, that reminds me of the character Easy Rawlins in Walter Mosley's books. 

@Amy DeCesare While the areas you mention could certainly benefit from more multi-family units, generally people in the more affluent parts of the state like Washington county oppose such new development, either indirectly through zoning ordinances like minimum lot size and parking requirements that make it almost impossible to build (as @Brandon Ingegneri mentioned), or directly at zoning hearings where neighbors show up and oppose it because that they don't want to change the "character" of their neighborhood.It can be done, but it's far more the exception than the rule and requires big bucks, political savviness, and the ability to make a big bet and absorb the loss if you lose.

It was on the market for a while, I actually went and looked at it with my agent and never made anything of it besides saying to my agent "what a beautiful old house with such character and craftsmanship lets look at the next property I don't like the numbers".

In my experience, it is very difficult to know the character of each neighborhood until you have been active in a market for a while.

I think you will see my profession shares some common attributes with yours.https://carlozgil.com/from-musician-to-investor/ If you are a musician or once were, reach out!

One thing I look for that is not related to whether or not if they can cover the rent is character.

If both houses are pretty much the same in character and the only difference is $100K in extra amenities, no matter the potential energy savings I would have, my key concern would be the upfront cost.

I am still living in the past, where your word is your reputation and your reputation is your character.

I have had friends of my son stay but their character and lifestyle was such that it could only be short-term.