I specialize in helping real estate investors implement insurance programs for their portfolios and would never suggest my client putting a single 4 family property on a commercial policy. 

If I did have a short term rental (we are in the market for one, hence the trip) I think I would post the additional cleaning and sanitation measures that are being implemented to ensure cleanliness of the rental in between renters.

That's exactly the strategy I want to implement.

i feel like me giving him my undivided attention and actually implementing the advice he gives me is somewhat of a "trade off" in his mind. 

Any other way will result in frustration or worse, it will find you chasing "shiny objects of distraction".To do this you must learn three things, and implement them as one. 

The conversions have been a great addition to help with building my portfolio and I'm happy that you are implementing the same.

Acquiring below market and implementing a value-add improvement plan will result in a portfolio of properties that appreciate over time and that also offer significant tax advantagesPick the right market – not all housing markets were impacted in the same way during the last recession.

I am planning on moving to Baltimore around February and would like to implement a house-hacking strategy, likely using a FHA loan.

I know they have recently implemented stricter guidelines for short term rentals but am unsure on how exactly the rules work.  

I work for one of those non-tech orgs which also has a DC presence...the new normal has already been implemented.