The lenders I have spoken with indicate if appraised as a one unit with accessory, it will work well. 

Check out building an ADU(accessory dwelling unit). 

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. 

Hi All -A bill was recently passed to allow Accessory Dwelling Units (ADUs) (<900 SF) to be built by-right in single-family zoning districts.https://www.mass.gov/info-details/accessory-dwelling-unitsMy understanding is that you could buy a single family home and build an ADU on it and rent it out. 

I could get stuck with a house full of substandard furniture and accessories that I need to deal with.

Disruption in global inventory supply chains has left stores with long lists of unhappy customers waiting months for bikes and accessories.

Many areas allow ADU (Accessory Dwelling Units) or In Law units, does yours?

Currently, you can add two units to any multifamily property through the state's ADU laws (ADU = Accessory Dwelling Unit).

Upon reviewing the zoning documentation, I discovered that the property was a single family residence, with a permitted accessory dwelling, and a permitted business office.

By the way, instead of a duplex, you might be able to find a single-family home with an accessory dwelling unit to use as a rental.