It is the policy design that matters.

Assume the unreduced basis of the building is about $350k (I took out the land value)*Add New Deck - $8k*Interior/Exterior paint - $3k*Dishwasher - $500*Landscaping materials - $1500*Wood/sheetrock to build walls to enclose an existing space - $500*Furniture (beds, tables, chairs etc) - $5k*Hot Tub - $5kCan we use the SHST or De Minimis or Routine Maintenance safe harbor for any of this? 

Home office deduction is available if you have a rental property and designated space exclusively used for rental property business.

They also help with operations as you can run them with one bank account and one set of books (if you manage the books properly by designating funds to each property).

Full disclosure - that is not what we have used, but it seems to get the job done.We did take the time to consult a designer on furnishings and got professional pictures, which seems obvious until you look at your competition, and our unit has booked within a week of listing both times that it has been available.

@Michael D Valadez, Unfortunately as you found, the Chicago Zoning Designations are a little odd in that the "3" in the RS-3 Zoning does not at all mean that it allows for 3-Unit residences.

Atlanta was terrible, but pretty sure I paid $20/night in a shared room so can't say much....My STR in Nashville was furnished by a designer.

Peeling paint on an older house needs to be fixed, windows need to open and close, fire alarms, dead bolts on exterior doors, etc. 

You do not want to violate the Dodd-Frank or SAFE Acts that require this designation.

Just got a new designated business mobile the other day through Verizon and I am super excited to get started!