This may affect value or time required to sell.7) Adding an ADU does not make the property a duplex.

You are required to calculate depreciation.If your net rental income is negative and your income is above $150,000 and the property is classified as passive, the excess loss will be carried forward to the following tax year.

In my experience, homes with window units only require a specific buyer versus having an HVAC which most buyers tend to prefer.

Did you include the required addendum for Carbondale? 

In Virginia you must give 60 days notice that you will not renew, check your state's requirements.

In a few of my markets (Philly for example), the minimum stay to be considered medium term is 31 days, anything under it is a short term stay and requires a STR license.

Given you have a disposed of asset, you would have a requirement to capitalize the new roof. 

By state law I’m only required to keep the heat at 68 degrees.

The cost of the materials was $1,500, and including labor I’d estimate this cost me about $3,000.The property manager never ran this by me or gave me an indication these project would be completed.Our service agreement is clear that written consent is needed when costs exceed $1,000 and in this instance these were not repairs and requirements needed to rent the property.

I am having trouble deciding if I should go ahead for a few reasons, one being that I would require outside investment and the cap rate could be as low as 4%, once rents are stabilized.