My first thought was an extensive TI package that was effectively financed into the rent.   

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. 

Being realistic, conversions to actual bookings are typically low.However, doing your research on potential travel influencers is key and understanding their packages & deliverables.

Is there a dollar value to knowledge and access, sure is, but $40k.... that price tells me the focus is on selling $40k packages not on the doing. 

Of course when an event was planned with food, why would I make a reservation?  

We even bought the same package for our Logan square property.In the first 3 months i made $175 dollars from 4 units.

For years i have had a portfolio policy with Nationwide for my commercial plazas but they are not renewing me this year as they now require all buildings with a food use to be fully sprinklered (which i do not have).

That's like asking, "Does food taste good?"

You are going to the job site and picking up the part and bringing it to return to the locker at Whole Foods or boxing up and driving it Idaho?

Just some food for thought, no two people have the exact same situation when considering this decision so do what you are most comfortable with.