The family we guaranteed rent to on their existing home, giving them the flexibility to buy with a partner builder and move out of state to be closer to the best treatment facilities when faced with a difficult diagnosis.10.

If you have an existing property that you've been renting out long term and want to switch it over to an STR to take advantage of this, is the IRS using the full calendar year to avg out the 7 day avg stay?

TLDR:  I'd say don't empty it until you know it needs to be emptied.Distilling your post, I see it as 1) you want to sell a property and 2) you see the existing furnishings as a liability

The idea would be for them to assume the existing loan and take my half of the property with as little burden financially on them as possible.

Check to see if reciprocity exists in the state(s) you’re considering getting licensed in.

BACKGROUND: Bought a property SUBJECT 2 an existing 1st lien (lets say serviced by Shellpoint) years ago.

I know it's zoned commercial but I will have to check with the city on what other restrictions might exist. 

The BRRR is one of the most complex investing strategies that exist.  

I'll be looking for a 'hands off' brokerage if such a thing exists (while realizing I'll need a 'high level of supervision' my first two years) with a low fee structure for my own deals.

The abundance of 2-4 unit properties in Chicago just doesn't exist elsewhere.