Hey Chris, a few thoughts here.Considering that office is not attached to the house, I wouldn’t add any footage to the total home square footage; however, you could advertise that office space and amount of footage and amenities in your remarks.If you’re a Realtor or are using one for the sale, your local MLS may have fields dedicated to additional footage for other buildings on the property, such as ADU’s.The other point is that typically, perhaps depending upon location, a space needs to have heating to count in the square footage, which this office doesn’t have if I understand correctly.Consider contacting an appraiser to inquire about how they would handle this space on an appraisal, or a Realtor.

Quote from @Daljit Singh: Unfortunately, you will have to play this out.

@Tinia JamesIf you receive a 1099 showing income from one of your deals, you have to file a Schedule C to report that income.

It depends on your loan.Your plan is to spend $50k to make $200-300k more a month?

Listing immediately at a bit of a discount to fill it quick on ST leases to reup in spring.

It only took me once to learn not to pre-approve a booking.  

CashHow did you add value to the deal?

Conventional financing How did you add value to the deal?

They become advocates, eager to refer others to join our network.

This often attracts broke tenants you will have to soon evict.