good medical at emergency!

I truly believe she had a medical condition and shouldn't even live in my house, should probably live in elderly housing or the like.

If you live in the home for 2 out of the past 5 years and move out of state you may be exempt from the tax.  

In addition, if this was originally an owner occupied house, there are often homestead exemptions where the first  $XX,XXX. of the value of the home aren't taxed.  

Some lenders allow exceptions for transfers to LLCs owned by the borrower, but it’s worth confirming first.Explore transfer tax exemptions: Chicago doesn’t make this easy, but there may be exemptions or reductions for certain types of ownership transfers.

If fully updated, market rents could be 5K a month plus utilities etc.The office space is currently being used as a medical office and it's a block from the hospital so there is always a good pool of rental candidates. 

In the past 10 years, Ocala has greatly improved the employment base, adding tons of logistics and distribution jobs on top of the medical, service and equestrian jobs that we have always had. 

You’d also make all future capital gains at least partially taxable instead of tax exempt by converting your primary to a rental.

In some cases that's amazing -- one part of the town gov't considers it to be a commercial lodging establishment so it's exempt from STR permitting and regulation. 

For example, I own two large multifamily buildings, and when I tried to get a tax exemption for them, I had different experiences.