I've helped numerous clients successfully purchase condos and houses as cash flowing STRs.

This amenity has attracted numerous buyers investing in million-dollar-plus villas arriving in private jets.

It means that if something is "added back" then it does not reduce the rental-income one reported; hence meaning more is applied as " rental income sources" towards bringing the DSCR numerator up...towards the 1.25x needed for loan approval odds.     

However, I'm somewhat concerned about managing numerous tenants, especially since I plan to rent by the room, which inevitably might lead to encountering a few challenging tenants.

The property is located in the Midwest and me and my business partner have ran the comps, numbers and called numerous property managers, handymen, inspectors and even asked locals on reddit to get a better understanding of the rental calculations and local biases in the area. 

I sent them a certified letter for an explanation.

I have made numerous claims, sometimes on the same property and my rates have never been raised.

I completely disagree with the advice given repeatedly above that you should have any sort of dialogue or explanation for a rent increase.

For me, if a manager is going to exceed the repair threshold on non-emergent repairs, they better do what I normally would've done or have a convincing explanation for why it was in my best interest.

Your explanation of rental property sale losses being capital (not ordinary) losses implies that it is not considered 1231 property.But IRS Publication 544 states:Section 1231 transactions.The following transactions result in gain or loss subject to section 1231 treatment.Sales or exchanges of real property or depreciable personal property.