Google 1205 Bartholomew for an example of a non-significant house that the HDLC would allow demolished with redevelopment plans, based on my conversations with HDLC (I was interested in this house 4-5 years ago, but decided to pass on it after my previous experience with HDLC new construction).I will say that doing work in any HDLC controlled area is a big pain in the butt and definitely increases costs.  

In the CBD (central Business district permit don't transfer but can be easily obtained (administrative).  

What if I invest it in more property and then the market tanks with the new administration? 

There are many penalties for landlords who violate the rules like you.It stinks and it's a pain in the butt, but we have to follow the legal system.

At a minimum the court is going to need to have somebody else assigned as the administrator or personal representative for your grandmother's estate.

It’s expensive and painful.

I'd say that's worth it although the new ordinance saying it say to be linked is a pain. "$200 lease filing, $200 admin fee, $200 sanitation fee, etc." is likely what you'll end up seeing.

It sounds like capital gains taxes will increase under the Biden Administration.

It’s two guys who are the owners, myself and an administrative assistant.

I would suggest doing this ASAP if you can as I worry that this loophole may close with the new administration so I'd jump on it.