that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Here's an article with things to consider when selecting a cost segregation company.

Does anyone have suggested property management companies they've used in Florida that they can recommend I reach out to, to see if we're a good fit for each other?

Water meter-water company.  

And the cost of legal defense , even if successful, will drive the company out of business.   

Now we're seeing major disasters in densely populated areas and insurance companies can't maintain their profit margins.

Sadly, on BiggerPockets, some are quick to label companies as scams without real experience.

He is making decent $, has a good 2.5 years of solid rental history.

Will they "check themselves" from bad behavior when they see a professional company with professional services, legally reviewed lease, etc. managing their day-to-day?

I didn't see a need for a holding company but if someone wants one, you can just use another LLC as the holding company.