One thing you definitely would want to keep in mind is knowing IRS rules and regulations as far as what you can and cannot do with your IRA, and make sure you do all of the due diligence you normally would as if you were using non-IRA funds.

Thank you.I would do the following: Assuming the contractor is still licensed file a complaint with the Illinois Department of Financial & Professional Regulation. 

I’m mostly concerned about following Covid regulations with the tenants through the sale process. 

In many states the cost of title insurance, the risk rate for the cost of the policy coverage, is regulated by the state either by the state promulgating the rate or by the title underwriter submitting the rate they intend to charge subject to the state's approval, known as file and use. 

@Mark Albini I've contacted a few local CU's, and many local banks, they all don't have the HELOC product on investment properties, and on investment property refi's go by the Fanny Mae regulations which allow 75% LTV based on the original sales price after 6 months ownership up to 1 year.

REITs are great because they are highly regulated; setting up a REIT is fairly cumbersome, which weeds out bad actors.  

I think that people forget that we are a heavily regulated profession and owe the same duties to our leasing-only clients that we do to our full service management clients, or a buyer/seller we are representing in a transaction.I think the bottom line is that there are unscrupulous individuals in any profession, and the vast majority of real estate agents ultimately want their clients to be successful and will work hard to that end.

I have thought about the appraiser field too after meeting the gentleman but its being squeezed by market forces and also by government regulations after the last housing crisis.

HELOCs are not regulated the same way that regular mortgages are, and this allows each lender to develop their own "rules" about when they adjust, what the interest rates are, and whether they lend against investment property. 

I feel like there is more than just getting the land and putting a house on it (Zoning regulations, surveyors, anything else).Any insight will help.