Looking for a business accountant in the Southwest suburb area of Chicago that knows about real estate investing regulations, business taxes, and 1031 exchanges etc.

Obviously you would want to check with local regulations before entering in to any real estate purchase.What do you mean 1/2 of the year?

If it is by chance technically “OK”, it appears to me to be skirting the intent of the regulations around disqualified persons.Who’s name would the 5th Maryland LLC be in?

Basically, anyone who had a pulse could get a loan.In today's market, lending regulations are still pretty strict. 

Not deal breakers.I'm currently an active retail mortgage originator, amongst a couple other things, but Its been my experience that working as a wholesale account executive from 2000 until 2016 and being on the backside of literally thousands of loan closings since the inception of the newest regulations that I can recall only one instance of a set back caused by cents on a transaction, but that was early on in the Dodd/Frank era and was the result of software, that was subsequently fixed by an addition 3 day waiting period, because that was the safest play for the lenders ***.The take away here, again just in my opinion, is on the front side of the transaction, write the offer at whatever it takes to get the contract done, then hand it off to your favorite lender...they'll figure it out. :)

I always recommend new hosts to establish in a city that already has regulation on them, yes you pay taxes on it, but it makes your investment more secure. 

Regardless, the Board adopted regulations that all but eliminated our options to rent the place, including a proposed $250 fee per rental for "administrative costs" and requirements that renters sign an extensive agreement about what they could and could not do on the condo common grounds. 

Setting up things the way you are means that you will need to learn 4 different state laws on short term rentals and property in general, 4 metro areas on STR rules and regulations, 4 different seasonal demand for STR rentals Not saying it can not be done but it will be harder than 4 rentals in one market.  

As far as Airbnb, as long as regulations are still favorable it might be a great addition.

She says this way I can regulate my gross income increase myself at the level that does not cause child support recalculation.I assume, this LLC option will require including LLC name on the house title, and refinancing the house.