One thought was to replace to large commercial tenant with a company that had a similar profile.

I don't see any reason why you would go to Miami, where the above problems are likely very similar, but there is even less cash flow to de-risk most investments, and it is not your backyard. 

Complicated post and I realize this might be more geared to a CPA, but figured I would try here and see if anyone else has come across a similar situation.

PropStream has now added something similar to D4D on their app

A property allowing one-night stays may be more prone to fraternity parties and similar.

If anyone has been in a similar situation or has actionable advice, I’d greatly appreciate it!

I've been wanting to expand out of my market in Iowa, and see that the Winter Haven, Lakeland, Haines City areas are similar to purchase points as my market.

However, if you seem similar listings in your area and they're requiring tenants put utilities in their name, then you should feel more comfortable doing so.

One word of caution: the court orders typically allow repairs to make a home habitable, i.e. rent-ready, but not cosmetic or similar non-essential repairs, like upgrades or additions.

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?