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 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.

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

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.

So, you can still get a conventional loan but the loan will require you to transfer the property to your personal name at closing. 

I've worked with clients that have had to put more money up front into the transaction because the specific bank they wanted to work with required it.