And I wonder if CCR or HOA can restrict these to protect the values of those homes ? 

We are selling one property in a location that has permits and other restrictions it would take Sherlock Holmes to find and when you inadvertently hit one there are fines plus the permits and delays. 

My thoughts are current housing supply + high rates + high home prices in OR are restricting our options and liquidating the brokerage to pay off the townhouse = $400k asset + $2,400 cash flow that we could then use to leverage or save into buying another property outright or scale into 4 plex and use the rent to pay down that mortgage too.

You Can Only Have 35 Non-Accredited InvestorsRule 506(b) allows an unlimited number of accredited investors but restricts you to only 35 non-accredited investors.However, there’s a catch:Non-accredited investors must be financially sophisticated.They must have enough experience to evaluate the investment risks.From the SEC:“Securities may not be sold to more than 35 non-accredited investors… [who] must meet the legal standard of having sufficient knowledge and experience in financial and business matters to be capable of evaluating the merits and risks of the prospective investment.”If you’re planning to include non-accredited investors, make sure they qualify—or you could be violating SEC rules.3.

Operating an Airbnb business requires being up to date on current local ordinances and restrictions.

Update, confirmed with the city and it is legitimate if the property is in the name of the LLC, and the LLC is grandfathered in before restrictions were put into place.

There is a big distinction on the variety of restrictions you need to be aware of with ADUs in Chicago specifically.

However, the challenge with MTRs lies in the CC&R (Covenants, Conditions, and Restrictions) and HOA (Homeowners Association) regulations.To proceed with MTRs, it's crucial to carefully review the CC&R to ensure that leasing out a portion of the lot to tenants is permissible.

•AE flood zones can limit your buyer pool because not all buyers want to deal with flood insurance or lending restrictions.

Self-Directed IRAs (SDIRA) or Solo 401(k)s allow tax-deferred or tax-free real estate investing, though they come with IRS restrictions.