Do you know if this would be an issue when it comes time to having my 5 year DCA inspection in ( mid 2025) as the property is only register with them as a 4 family?

You cannot even apply for an STR permit on a single family home until after you've owned it for five years (and there is no guarantee you will get the permit).

I even try to unsell them on the business by sharing my financial losses, litigation,  market shifts, permit purgatory, shady contractors,  clouded title issues,  paranormal activity, squatters, mold, etc.

Getting a bit overwhelmed with all the required County Level and City Level business licenses, STR permits and Tax accounts (Business Tax, Franchise & Excise Tax, Sales & Use Tax) to register with the state.

They may also be able to temporarily relocate your tenant to avoid any other issues.

There are two issues (opportunities?) 

The permits and architecture was done prior to start.).For most people the finances are the limitation to scale.  

do you know how to read building plans or permits?

The location is ideal, as it’s situated in a neighborhood that permits short-term rentals (STRs), making it a great investment opportunity.

The townhouse is located in Aspen’s sought-after lodging district, where STRs are fully permitted.