According to a Google search in my market landlords are not required to do any of the above.

That being said the tenant is required to notify you in writing 30 days prior. 

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

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

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.

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

Is he required to issue me a 1099 form for rental income for 2023 taxes?

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.