u/Badluckwithlove

I’m in Florida and looking for legal guidance regarding a former friend. I’m trying to distance myself from him, but he continues contacting me and I’m becoming afraid of retaliation.
He previously lent me a phone when I needed one. I returned it last year. Recently, around 1 a.m., he texted me:
“Who’s Ma-ICE? Her number is on the phone and a lot more. You sure you reset that phone?”
“Ma-ICE” is my mother. I’m concerned that he went through the phone and accessed or retained personal information that was mine. I don’t know exactly what else he accessed.
There is also a financial issue between us. He claims I owe him money, and I have agreed to make payments. Because of this, I have continued communicating with him at times even though I don’t want a personal relationship or to see him.
I have not yet told him that I want communication limited to payments, but I want to establish that boundary. I’m concerned that doing so could make him angrier because he has previously made statements that caused me to fear he could send other people to hurt me.
There has also been other concerning behavior, including repeated unwanted messages, false accusations, insults, and sexually inappropriate messages. I have screenshots of these communications.
My questions are:
Could accessing my personal information from the phone be illegal in Florida?
Could the overall pattern potentially constitute harassment or stalking?
Do his previous threats matter for a protective injunction?
Does the fact that I sometimes responded because of the money issue affect my ability to seek protection?
What is the safest/legal way to tell him that I will only communicate about payments going forward?
What evidence should I preserve?
I’m not looking for revenge or for anyone to contact him. I’m trying to understand my legal options and how to safely establish boundaries.