But...If the average renter is being left behind, if their income can't stay in line with the cost of living, I fear it will lead to a larger crisis and continued intervention/regulation by government.  

Do you know the regulation for Florence?

If you're established enough as an investor that you're already doing projects and own assets, it's highly likely that taking the time to save 10 cents per letter by doing it yourself is not worth your time.

For extra insurance, you may want to start giving 10% of your bookings to another cleaner to establish a relationship in case anything happens with the 1st cleaner. 

I have a realtor friend that knows the Miami STR regulations like the back of her hand.

Hi Sam, I would highly recommend reach out to your county or city government to get accurate STR regulations before you list it on Airbnb & VRBO. 

Does anyone have any recommendations for how to collect monthly rent payments digitally into an established account?

Lenders have to meet additional regulations if you plan to live in the property which is likely why you are continuing to get that question.

Understanding cash cycles from different marketing channels will give you a better understanding of which path will be best for you to pursue.Outbound channels are getting more and more regulated as days pass, so I recommend diversifying with different marketing channels so that when one gets shut down, your business doesn't suffer significantly.

I'd love your insights on which cities you think are ideal for multi-family properties, especially in states with landlord-friendly regulations.