We have also been in this house 4.5 years and just learned about the new tax rule pertaining to this. 

If the purchase in question is a Co-op apartment, there is also a Co-op attorney involved in the deal.I'd say, that is the first layer of red tape.Depending on the property type and deal, the other red tape here pertains to zoning, permits, land use, environmental regulations, rent regulation i.e. rent control, rent stabilization, etc. to name a few.Wishing your company continued success as you look to expand!

As a pertains to the question, in my experience, tenants always taken advantage of scenarios like this, whether it’s warranted or not. 

They have proven over the years to be cheerleaders rather than true economic analysts.But overall, get the raw data that pertains to your area and follow what it says.

Check if the city has any MTR/STR restrictions pertaining to only multifamily. 

Doesn't pertain to the question but, I always use lighter color floors to help minimize the wear look. 

I'd recommend that your mom talk to a financial advisor before looking for the CPA, to have a conversation pertaining to whether these proposed investments align with her goals, risk tolerance, and diversification requirements.

@Shanel Dial what new AirBnB Chicago laws would you be pertaining to that hinders you from continuing your STR business. 

Originally posted by @Megan Clancy:I’m not recommending an FA, I just wanted to point out that the fiduciary law actually went into effect on June 9, to be gradually implemented over the next 1.5 years and go into full effect on July 1, 2019.The Department of Labor fiduciary rule only pertains to retirement accounts covered by ERISA - 401K, IRA, etc.

From there, I would also check the population growth, what industries are affecting the areas, and any other local information that might pertain to your niche.