I need a good insurance broker to insure a vacation rental. 

Residential class is just a lot easier to do the financing and the insuring, and you're not getting much more scale at 6 units.The downside is that you won't be able to directly capture any forced-appreciation on residential class (4 units and below.)

What type of insurance is recommended for the business?

I own several rental properties in the Cleveland Area and I also own a local insurance agency.

This is a job requiring permits, license, and insurance.

E - 1/1 $450 lease from 7/26/2006 - Middle aged male likely to continue to stay for an extended time.Taxes on the building would be roughly $2500, Insurance estimate $1200.

I would take a 2 or 3 quarter view of your average maintenance and see what projections you come up with to be sure the job you'd be hiring for is actually stable on your first go at this. 

I am considering lending in second position, but requiring a quick claim deed to the property,  as insurance, and if borrower fails to perform on the first or my 2nd position note, then file the deed and take the house. 

Things such as 401(k)’s, IRA’s, and life insurance policies have beneficiaries.

Hire an exterminator.And get rid of the bad tenants now.As far as animals, I require renters insurance, I don’t know the law in FL, but in WI if a tenants dong bites someone, and they don’t have renters insurance, the victim can come after the property owner