Many people will advise that you should issue 1099's, but what I wanted to know (and it sounds like you do too), is whether you are required to issue them. 

Sounds like a wonderful project.

The strategy sounds fine but will be a slower process (time) as well as more expense with your cash being tied up inside each property.I'm a fan of the  BRRRR method, where you use debt to create assets and then have the renter pay your debt off over time.

Will need premium luxury space build out to make this move complete with private sound proof office partitions and key faub security protocols installed. 

If this is in the Atlanta metro area, that sounds pretty low and could very well be in a rough area.

@Nick Hakim - I am not a lawyer, but it does not sound like a grey area. 

But you know its as simple as it sounds.

They don't disturb me, they don't knock on my door or ring my bell. 

It sounds like you will exceed this, though.If you are a RE professional, as J described, the activities that were once considered passive (rentals) are now considered active, in which case you can use the losses to offset your other income (flipping income).Your flipping hours count towards the 750-hour requirement to become a RE professional.

This sounds like a separate dwelling structure that is not within primary residential dwelling space.