Not sure if I should structure as a traditional home sale + a separate business package including all accessory structures, furniture, biz ops, STR license, etc.Maybe as an add on if someone wants to use it as a hostel business as well but still open to a traditional buyer purchase separately. 

If you see a 6 unit that has 2 separate units both listed for rent and it's not remodeled, probably a higher chance of landlord fatigue.  

Do I need to get a separate contract drawn up?

Either work but in Metro Atlanta, the easier option is an SFR with roommates or potentially separating the basement as a separate lease space. 

If they have a thermostat in their unit, that means they are a separate zone on the gas heat.

Open a separate checking account dedicated to marketing and budget 6 months of mail, so if you have $6k, you would do $1k per month with 1/4 of that dropping every week.

As a general rule, each entity that files a separate tax return (partnership, s-corp, c-corp, etc) will need its own QBO subscription.

I want to separate the size into maybe four groups.

Do I have to complete the separation of units by January 1st to write off half of my closing costs/other expenses?

@Max Bellino if you feel the need to interview six separate attorneys for this scope you are over complicating your true needs.