First off I haven't been too pushy. When it is a simple case of the Marine Police coming up nicely and advising, I would say I wasn't planning on staying more than three days. They are generally pretty easy to get along with. However, you can also get latched on by a true Nazi, in which case, I move - it isn't worth it to me to spend my money and time in a place that doesn't want me or my money in a polite manner.
Where a landowner has called them they have been professional and polite. They also have told me I am fine where I am and if the town has a limit they tell me about it. They have also told me where the best dinghy dock is. My impression is the majority are doing their job and not trying to be a hard ass. I've even had them ask if I've had any trouble, while looking at, or quietly pointing at a particular pier.
The problem seems to be the waterfront property owners don't want their view disturbed. My approach is if I'm hassled, or hard assed, I leave. Life is too short and we are supposed to be enjoying it.
Other than it being warm in the winter, Florida has no appeal to us. We prefer heading north in the summer, better scenery, better sailing and friendly people.