Conventional lenders will require 12 months on a cash out refinance while DSCR lenders do not have a seasoning requirement. 

Am I still required to send a security deposit statement showing the amount they owe to me? 

I own an Airbnb in a desirable vacation rental market.

A friend and I recognized that we both have a passion and desire to pursue rental investing in our future.

They're going to require that you file a form with them every single year (it's Form 3840) and on this form you need to report back that you still own the new investment property, and that you haven't sold it and haven't received the income from the sale. 

Fannie/ freddie have different guides on this, and i do see different lenders interpret them differently. for example, one requires you to OWN your primary residence in order to use rental income on the subject MF, the other will let you do rental income from your MF subject property with a "present housing expense" (rental housing expense being ok) so long as you have a 1 year + history of landlording (which it sounds like you do). maybe ask your mortgage pro if they are giving you credit for rental income from the subject property units?

Negotiate purchase price and financing terms aggressively to secure favorable terms, exploring different financing options like FHA loans, VA loans, or conventional loans with low down payment requirements.

The estoppel will probably require you to make contact with these tenants and come up with an end date on the lease.

However, I recently got an offer letter that will require me to be on site.

What Insurance coverage you need to require of the Pharmacy in the lease (General Liability, Professional Liability, Environmental/Pollution Liability, Business Auto, Workers Comp., Umbrella Liability.