I have personally been involved in house hacking and furnished rentals for over five years, and it's been fascinating to see the quality of mid-term tenants we've had over the years.However, it's worth noting that in our area, the demand for short-term rentals on platforms like Airbnb and VRBO has declined in the past 24 months.

It's your property and investment.Of course you don't want the maintenance person taking your $300 set of a steak knifes.  

Personally we have had great experience so far.

Did the pest control person seem to indicate an infestation? 

House hacking will also give you some personal "property management" experience.

- How many personal use days (sometimes including family or other discounted renters) do you plan to have? 

Thinking about taking a little cash out, mixing it with personal savings and going after another property with a nice down payment as a hedge against market fluctuations. 

I’m personally happier entering into longer leases, even though they purport to offer premiums over market rents.

If we chose to convert it to rental, and keep all that money completely seperate from our personal finances, do we do it all in his name? 

And you likely haven't faced life on a downturn, it all comes down at once and it's kind of correlated professionally and personally.