Primary residence exemption - the portion of the property that you live in is eligible for the primary residence tax exemption after you reside there for two of the last five years.

Can I sell it and get an exemption to the capital gains tax of occupying the primary residence 2 of the last 5 years?

@Chris Williamson, you don't really need a CPA for that because there are no tax implications with the rollover, and like I mentioned earlier all investment income will be sheltered from taxes since it is an IRA, unless you have income from active business or use leverage to acquire investment property (btw, self-directed Solo 401k would be exempt from UBIT on leveraged real estate).

There are stuff like medicaid annuities and exemptions that the parents can look into.I'll see if I can find you a referral.

On one end I read about investors that take advantage of the Act 22 tax exemption, on the other end the government struggles with debt and reconstruction of Hurricane Maria damages.

Unless this note is being held by a non-owner occupied investor, then you may also be faced with ursury exemption limit on the interest rate depending on the state its held.  

Only other thing to worry about is estate taxes which at 10M exemption don’t apply to most people

Perhaps I missed it and would love to see where in the bill it states that capital gains must be used. https://www.congress.gov/bill/115th-congress/house-bill/828/text#toc-H2CE36B67ACCC4F89BD0B2571450C0176The portion of an OZ fund interest attributable to any capital invested in excess of the qualified gain amount is not eligible for the OZ tax exemption. 

Except that no exemption applies to any real estate licensee.In other words, these things really do vary by locale.

Oakland has strict rent control laws, like San Francisco, Berkeley, and many other cities, however there is an exemption for both duplexes and triplexes when the owner lives there as their primary residence.