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

Keep receipts and records to substantiate these expenses.The IRS allows you to deduct 50% of qualifying business-related meal and entertainment expenses.

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. 

I'm the principal broker for Hardin Realty & Property Management -- We encourage agents to invest and complete personal transactions!

They know how to track things, use multiple PMS softwares, file aircovers and so much more because I have personally spent years training them exactly how to do things the right way. 

Meetings are once a month in person and many meetings on zoom.

While this is a real estate forum, personally I do not see buying real estate right now a great investment.

Quote from @Jerryll Noorden:MAYYYYBE  interconnect 400 super comuters together and feed it every single piece of data on this planet and construct a real life emulator/simulater with every person's artifical character on that simulation where every user has inputter their life's journey...