I know a couple guys in my home town that served 5+ years in a federal prison for this.If you're moving ownership into a land trust that you also control and have no intention of defaulting or selling and avoiding the payoff, it could for sure be argued as positive fraud, but the intent would more likely be for something like asset protection or some kind of investment arbitrage - which could still be fraud.  

The parents can complete a 1031 exchange in their name and then after the fact contribute the property to a new entity under their control as long as the contribution does not trigger a "sale" event. 

Private equity backed by a promissory note is considered a “bond” which is considered a "security outside of my broker/dealer's control” which is a big no-no if I am registered with them.

I don't think any changes will be made to rent control.

You can do that with self-directed IRA, or better with truly self-directed Solo 401k plan, which has significantly higher contribution capacity (get the max tax break now), does not require a custodian and offers you checkbook control over your account (just some of the benefits). 

@Darren GregoryYour friend refers to a very old (and long dead) rule, which is why it's best not to ask friends for legal, tax or medical advice :)There are only two ways to control capital gain taxes on selling your own home, and they can be combined.

You should consider holding all Real Estate in an Illinois Land Trust with a business entity you control as trustee.

After done renovations / repairs / maintenance on many many properties, I kind of know the price range of each job like painting, flooring, drywall, plumbing, electrical, AC, pest control, remove odor from old pet urine, mold remediation, cabinets, countertop, backsplash, appliances etc etc in my mind.

The disclosure specifically says no water leakage, accumulation or dampness as well as no repairs or attempts to control any type of water.   

In those cases, the tenant gets what they want and feels appreciated and we still maintain control of improvements to the property.