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?

In this option your agent would either get paid from you directly in your closing costs OR from the seller via seller concessions.like Russell said, if you are comfortable with the transaction and understand what you are signing and you don't need things explained and you have connections with inspections and title companies then go for it.

My recommendation would be to get approved as a Landlord, contact the director's office and request that an inspection be completed before a tenant is selected (sometimes they will do this as long as you select a tenant within 14 days - which you want anyways), and have an online application and screening resource in place.  

The upgrade basically put a target on my back with the fire marshall as he came by to inspect the work and found that there were a few compliance issues.

First, I schedule an inspection, quickly.

In hindsight I probably should have gotten an additional HVAC-specific inspection and tested the measurements for the actual washer/dryer space.

A truly "motivated" seller tends to not really care the amount of earnest money and you could also structure your EM due at end of your inspection period. 

I even called the number at the end of the webinar to ask how earnest money works, which they claim they pay upon completion of inspection.

Don't get into an argument with the listing agent over how their price is wrong or over inspection issues4.)

I'm out of pocket over $5k in EMD feels, appraisal fees, inspections and almost 2 months.