The Importance of a Great Real Estate Agent: A Personal Paradigm ShiftI got my real estate license a while back, and I always heard people talk about the importance of "bringing value" as an agent or broker.

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.

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 instance, many tribal lands are exempt from state and local property taxes, which can obviously lead to significant savings.

You’re going to be personally sued no matter the cause of the loss.

Once you take over a property as an owner occupant, if it is a single family or condo you can live in it for 1 year and that automatically exempts your unit from rent control.

So I contacted the tax collectors office and was told there was a legal loophole and that since the building had been owned by a non-profit for part of the year it would receive tax exempt status for the full year.

SFHs are largely exempt from many regulations such as rent control.

There is an amount that you can distribute from an IRA account to purchase a personal residence.You then might be able to turn the personal residence into an investment property.Best of luck.