As well as if it is smart to even have this as a back up plan In most places tax liens go right to the front of the line so there's no real risk to the state/local government and thus no reason to sell them for pennies on the dollar, as they usually can collect everything just by foreclosing.

@Kim LeJeuneIf you lived there and sell shortly after (within 3 years), you may not owe capital gain tax.When you ask about the form, it sounds like you intend to wrestle with forms.

If you already own it and it was a personal residence that you don't want to sell providing you live somewhere in the area, have an interest and understanding of your local rental laws and aren't in California (the laws) or Florida (the possibility of assessments) then self management is a possibility. 

My question is, should I sell it now and make $500k+ to reinvest in multiple other properties or wait the unknown amount of time for the property to be sub-dividable and potentially make 3-4x?

Or should I even just cut my losses and sell.

I think it would be a great house hacking plan for you.As far as your exit plan goes, selling a property with an ADU isn't always straightforward.  

I am not a seller because I am not selling anything.

thanks Note that there is no way to sell your shares as of yet. 

I'm trying to learn more about capital gains tax when selling a rehabbed home or refinancing for the equity.

Why hold in Baltimore when you can hopefully get it vacant, sell it, and use the money for another property closer to you or use that money to build an ADU.Have you checked the regulations on ADU and impervious cover for your house?