Your insurance may also not cover you or your tenants. 

I have high revenue from my rentals and have diversified other investments that cover my lifestyle.  

Make sure you have adequate reserves to cover unexpected emergencies.3) Time-intensive - If you live on-site you're a live in property manager on call 24/74) Legal issues - know the max occupancy laws for your area.

Not every state or city mandates that any landlord has to accept Section 8, because the landlord has to not only subject their property to Section 8 inspections, rules and regulations, they also often have to separately arrange for the tenant to pay the non-covered part of the rent and can face difficulty evicting just based on that.

If they are taking out a few breakers and a fire happens insurance will typically not cover anything.

Will the cash flow even be able to cover that?

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

I would venture a guess that many investors believe that agents who cover the same territory are competitors, however as I'm sure you are aware that there is more success in collaboration as agents than competition.

Think beachfront condos that not only cover their costs but actually give you solid cash flow.

I handle St Augustine/Ponte Vedra/Palm Coast but can certainly help with Jacksonville and based on your goals there may be other opportunities to explore.To cover off insurance from previous comments, the market has changed and it is competitive with new carriers entering the market.