But the lesser grade lumbers like #2 offer a great value and the irregularity can add tremendous character to your rental. 

I know roaches MAY be attributable to the cleanliness of a home, but I do not believe that bedbugs exist due to any fault of a tenant.

There is no capacity for making contributions to an IRA in-kind, and the IRS certainly has no interest in trying to properly attribute value to an individual's services as contributions - so much room for mis-interpretation and malfeasance....

I love old houses with big moldings, cool original details and some character.

Your property seems to have some attributes that set it apart from others which would make finding comps difficult. 

If they were approved by a bank to buy an $850k home last year, now selling that home for a gain, I know them and have positive experiences and believe they have solid character, we were neighbors for a while, their young girls are very sweet (and occasionally very helpful with yard work) ...why would another background check be required?

Based on it's location I think it needs to be something with a bit more character than a franchise in order to be successful. 

I have a couple of properties that were part of larger trades and their attributes are different than SFR.

Taxes attributed to rental properties are reported on Schedule E or Form 8825 for an entity.

Not much use in August and September but it doesn't change it's character and become non-investment during those months.