I am also  open tot help others with their real estate needs here as well! 

I bought a primary residence last October that I planned on renting out come this October (next month) and would love some advice from more experienced folks on my next steps, because I came up with a few options. 

I've been told that it helps with the Airbnb algorithm.

The local building department might require this.

Talk with your lender about this proposal...  1) Get a solid quote on the roof replacement and share it with your lender.    2) Put the funds in escrow with your bank for the sole purpose of replacing the roof.    3) Close on the property.    4) Install the roof.    5) Get reimbursed for roof expense out of escrow.Most banks are fine with something like this if they know their downside is covered.  

A seasoned CPA with REI experience can help ensure all your passive losses are applied correctly and provide guidance on future sales.

How we helped a resident, who lost their spouse, buy the home they were leasing to make sure his children felt stability and at home! 

HOWEVER, BP friends that are in this space right now, what should I ask about when I do speak with the owner?

:)I'm strongly considering it at the moment, and I might end up starting on their service by the end of this week or early next week.

I realized that this was the path for me to be financially free.