Hey Diesel JD,
We packed up our bags last year after Charlie hit and opened a sattelite office in the Punta Gorda Area.
The best way to answer your question is...it depends. Depends on whether you are just pruning or doing removals, planting trees or digging stumps, installing irrigation or....just too many possibilities.
It alos depends on which county and which town/city you plan to work in.
Anyhow, speaking just for us and our situation, we are staying strictly with pruning and removals and are apparently exempt from requiring the State Issued Contractors Licence
It is my understanding, though, that as soon as we put a hole in the ground, either to plant or dig a stump, that we would then be required to get that license. Not really a big deal, just have to sit for a couple of exams, pass them and then pay a licence fee.
Next, and each county is different, our base county requires us to have an occupational license. This is simply a business registration tax. It varies in cost but it gets you on thier books.
Now, there are some cities that have further licensing requirements. One of them happens to be North Port. They require a "Certificate of Competency. Which, after trying to figure out the paper work, apparently amounts to nothing more than a credit check. However, because the town administration seemed to have thier noses in the air and the paperwork involved seemed so ominous, we decided to not even bother working/advertising in that town.
As for insurance, carry your standard coverages. But, be careful, getting tree service coverage is not the easiest, nor cheapest. Work with a good agent. We have some people from Farm & Family who seem to be very good at finding the small guy coverage. you might check to see if they write policy down there.
FL has different Workers Comp laws too. Keep that in mind.
Hope this helps!