If it is a residential property you should do some due diligence like check for liens, call town code officer and check map and deed if available.

I also checked with the local clerks office and the lien index.

There is often a disconnect between how things work on paper versus in the real world...Funny story, I had a tenant who became a police officer, which was probably the third profession he had tried since being a tenant.

(5) and finally, do you all have recommendations for loan agents / officers who can help us think through what would be the optimal path for us given our situation?

Lucie4) Nashville5) Raleigh, N.C.6) North Point-Sarasota-Bradenton7) West Palm Beach-Boca Raton-Delray Beach8) Punta Gorda9) Spokane-Spokane Valley, Wash.10) Olympia-Tumwater, Wash.Florida boasts five of the top 10 markets with the strongest commercial markets – a ranking that includes the apartment, office, industrial, retail and hotel sectors – according to the National Association of Realtors® (NAR) Commercial Market Conditions Index rankings for the second quarter of 2021.To find out more, check out this article from the FL Realtors 

Risk is higher mainly because it relies on your skill and intelligence to be successful in real estate.

Gave the office a call yesterday and have yet to hear back.

They come and go.You could ask to see a copy of the most current property tax bill during due diligence.The market value of a commercial property may be based on the market cycle of current rent rates, not assessed value from the county assessor's office. 

I would ask other mid to top  producers in your office to help you out.

Push credit and debit card payments hard, to make life easier for you (auto-payments), and make cash payments very difficult to do and/or not accepted (eg no office onsite, etc).