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.

I cannot argue with a straight face that the market value fluctuates monthly and equates the actual monthly collection.The overall idea of using an S-corp to control SE tax is valid, but it needs to be implemented differently. 

@Mike Loy, As a realtor you qualify for a Solo 401k, which has many advantages over self-directed IRA, here are few:Contribute 10X more than into an IRA (up to $61,000 per year per participant)Access up to $50,000 from your retirement account tax-free and penalties-free at any time prior to retirement via participant loan featureExempt from UDFI tax on leveraged real estateInvest tax-free using Roth 401k sub-accountCheckbook control without use of an LLC Custodian is not required = no custodian, transaction or asset based feesYou can read it in more details here:https://www.biggerpockets.com/blogs/2810/21298-sol...The bottom line is that if you qualify for Solo 401k - it would be way better than an IRA.